Triethylamine → (S)-9-Chloro-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzoxazepine-5-one
Reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].C(N(CC)CC)C.[NH:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][OH:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[Cl:1][C:2]1[C:3]2[O:25][CH2:24][C@@H:20]3[CH2:21][CH2:22][CH2:23][N:19]3[C:5](=[O:6])[C:4]=2[CH:8]=[CH:9][CH:10]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
To a solution of 3-chloro-2-fluorobenzoyl chloride (2.2 g; 11.4 mmol) in di-methylformamide (5 ml) was added triethylamine (1.7 mL; 11.7 mmol) and (S)-(+)-2-pyrrolidinemethanol (1.13 mL; 11.4 mmol). The mixture was stirred for 1 h then caesium carbonate (7.4 g; 22.7 mmol) was added and the reaction heated at 120° C. for 5 hours. The reaction was cooled to room temperature then diluted with water and extracted with ethyl acetate The organics were washed with water and dried (Na2SO4) evaporated in vacuo. The crude product was purified by chromatography on silica (eluting with 5% methanol in dichloromethane). On removal of solvent the pure amide crystallised and heptane/ether was added and the title compound collected (0.26 g). M.p., 89-90° C.; EIMS: m/z=238 [M+H]+
Workup
- temperatureThe reaction was cooled to room temperature
- extractionextracted with ethyl acetate The
- washorganics were washed with water
- dry with materialdried (Na2SO4)
- customevaporated in vacuo
- customThe crude product was purified by chromatography on silica (eluting with 5% methanol in dichloromethane)
- customOn removal of solvent the pure amide
- customcrystallised
- additionheptane/ether was added
- customthe title compound collected (0.26 g)
- customM.p., 89-90° C.
Sources & evidence
- ORD record
- ord-5ae1bc8b91564d71ba3ac5690d90d017
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07307073B2
Reaction notes
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