InChI:InChI=1/C18H16BrNO3/c19-10-15(21)13-6-8-16(18-14(13)7-9-17(22)20-18)23-11-12-4-2-1-3-5-12/h1-9,15,21H,10-11H2,(H,20,22)/t15-/m0/s1
The targeting of both the muscarinic and...
An improved process for the preparation ...
The invention provides a class of compou...
The present invention relates to 8 - ben...
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one
8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one
Conditions | Yield |
---|---|
With (S,S)-1,2-diphenyl-1,2-diaminoethane; hydrogen; potassium hydroxide; In isopropyl alcohol; at 25 ℃; under 3800.26 Torr; Solvent; Pressure; Temperature; Autoclave; Inert atmosphere;
|
99% |
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at 0 - 30 ℃; Inert atmosphere;
With hydrogenchloride; In tetrahydrofuran; at 0 - 30 ℃;
|
95% |
With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at 0 - 10 ℃; Inert atmosphere;
|
95% |
With dimethylsulfide borane complex; (1R,2S)-1-Amino-2-indanol; In tetrahydrofuran; at 20 - 25 ℃; for 3.5h; Inert atmosphere;
|
85.5% |
With Trimethylboroxine; (R)-α,α-diphenylprolinol; In toluene; at 20 - 150 ℃;
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With borane; In tetrahydrofuran; toluene; at -10 ℃; for 4.75h;
With methanol; In tetrahydrofuran; toluene; at -10 ℃;
|
81% |
With borane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -10 ℃; for 4.75h;
|
81% |
(R)-α,α-diphenylprolinol; With Trimethylboroxine; In toluene; at 20 - 150 ℃; for 4.5h;
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With borane; In tetrahydrofuran; toluene; at -10 ℃; for 4.75h;
|
81% |
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With borane-THF; In toluene; at -10 ℃; for 4.75h; Cooling with isopropanol-ice;
With methanol; In toluene;
|
81% |
With Trimethylboroxine; (R)-α,α-diphenylprolinol; In toluene; at 20 - 150 ℃; for 4.5h;
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With trimethylborane; In tetrahydrofuran; toluene; at -15 - -5 ℃; for 4.75h; Cooling with ice-isopropanol;
|
81% |
With borane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at -10 - 5 ℃; for 4.75h;
|
81% |
Trimethylboroxine; (R)-α,α-diphenylprolinol; In toluene; at 20 - 150 ℃; for 4.5h;
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With borane; In tetrahydrofuran; methanol; toluene; at -15 - -5 ℃; for 4.75h; Cooling with ice/isopropanol bath;
|
81% |
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With Trimethylboroxine; borane; (R)-α,α-diphenylprolinol; In tetrahydrofuran; toluene; acetonitrile; at -15 - 20 ℃; for 5.25h;
With methanol; In tetrahydrofuran;
|
81% |
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -20 ℃; for 4h; Inert atmosphere;
With methanol; In tetrahydrofuran; toluene; at -20 - 20 ℃; for 0.333333h;
With hydrogenchloride; In water; at 20 ℃; for 18h;
|
76% |
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With dimethylsulfide borane complex; In tetrahydrofuran; toluene; at -20 ℃; for 3h; Inert atmosphere;
With methanol; In tetrahydrofuran; toluene; at 20 ℃; for 0.333333h;
With hydrogenchloride; In water; at 20 ℃; for 18h;
|
76% |
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at -20 - 20 ℃; for 4.33333h; Inert atmosphere;
With hydrogenchloride; In water; at 20 ℃; for 18h;
|
76% |
With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at -20 ℃; for 4h;
|
76% |
With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -20 - 20 ℃; Inert atmosphere;
|
76% |
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -20 ℃; Inert atmosphere;
With dimethyl sulfide borane; In tetrahydrofuran; toluene; at -20 ℃; for 4h; Inert atmosphere;
|
76% |
With borane dimethyl sulfide complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -20 ℃; for 4h; Inert atmosphere;
|
76% |
With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -20 ℃; for 4h; Inert atmosphere;
|
76% |
With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -20 ℃; Inert atmosphere;
|
76% |
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With dimethylsulfide borane complex; Trimethylboroxine; (R)-α,α-diphenylprolinol; In tetrahydrofuran; toluene; at -6 - -5 ℃; for 3.5h;
With methanol; In tetrahydrofuran; toluene; at -5 - 0 ℃; for 0.5h;
|
|
With borane-THF; Trimethylboroxine; (R)-α,α-diphenylprolinol; In tetrahydrofuran; toluene; at -10 ℃; for 4.75h;
|
95 % ee |
With borane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at -5 ℃; for 3.75h;
|
|
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at -55 - -45 ℃; for 0.666667h; Inert atmosphere;
With borane-THF; In tetrahydrofuran; at -45 - 0 ℃; Inert atmosphere;
With methanol; In tetrahydrofuran; at 20 ℃;
|
|
With formic acid; C25H29ClN2O3RuS; potassium formate; In chloroform; at 25 ℃; for 24h; enantioselective reaction; Inert atmosphere;
|
94 % ee |
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; In tetrahydrofuran; at 40 ℃; for 48h;
With borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -10 - 0 ℃; for 4.5h;
|
|
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one; With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at 0 - 2 ℃; for 3.25 - 3.33333h;
With methanol; In tetrahydrofuran; toluene; for 0.25 - 0.333333h;
|
8-benzyloxy-5-bromoacetylcarbostyril
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole
8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one
Conditions | Yield |
---|---|
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; With dimethyl sulfide borane; In tetrahydrofuran; at 0 ℃; for 0.166667h;
8-benzyloxy-5-bromoacetylcarbostyril; In tetrahydrofuran; at -10 ℃; for 0.333333h;
With dimethyl sulfide borane; at 0 ℃; for 5h;
|
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one
8-benzyloxy-5-bromoacetylcarbostyril
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole
8-Hydroxyquinoline-N-oxide
8-(benzyloxy)-5-[(1R)-2-bromo-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]quinolin-2(1H)-one
(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
4-({[5-(2-{[4-({[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}methyl)phenyl]carbamoyl}ethyl)-2-phenylphenyl]carbamoyl}oxy)-1,1-dimethylpiperidin-1-ium trifluoroacetate