Benzyl chloroformate → (1R,5R)-3-Benzyloxycarbonyl-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid methyl ester

HRID 1917331Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:12][O:13][C:14]([C@:16]12[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:19][N:18](CC1C=CC=CC=1)[CH2:17]2)=[O:15]>ClCCl>[CH3:12][O:13][C:14]([C@:16]12[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:19][N:18]([C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])[CH2:17]2)=[O:15]

Participants

Conditions

Temperature: 40 °C

Procedure

Benzyl chloroformate (3.53 mL, 24.6 mmol) was added to a solution of (1R*,5R*)-3-benzyl-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid methyl ester (4.27 g, 16.46 mmol) in dichloromethane (50 mL) at room temperature, and the mixture was stirred on an oil bath at 40° C. for 23 hours. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→80:20→67:33) to give 2.24 g (45%) of the title compound as a colorless transparent oil.

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→80:20→67:33)

Sources & evidence

ORD record: ord-85ac0279b792423298a5545fc769e049
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618094B2

Reaction notes

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