Benzyl chloroformate → HCID 67490919, compound

HRID 1917353Notes

Reaction equation

[C:1]([O:5][C:6]([C@@:8]12[CH2:15][CH2:14][C:13]([F:17])([F:16])[C@@H:12]1[CH2:11][N:10]([C@@H](C1C=CC=CC=1)C)[CH2:9]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:26]([O:33][C:34](Cl)=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[C:1]([O:5][C:6]([C@@:8]12[CH2:15][CH2:14][C:13]([F:16])([F:17])[C@@H:12]1[CH2:11][N:10]([C:34]([O:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:35])[CH2:9]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

{(1S,5S)-6,6-Difluoro-3-[(1R)-1-phenylethyl]-3-azabicyclo[3,3,0]octan-1-yl}carboxylic acid tert-butyl ester (370.0 mg, 1.05 mmol) was dissolved in dichloromethane (3 mL). Benzyloxycarbonyl chloride (898 mg, 5.26 mmol) was added, and the mixture was stirred at 40° C. for 17 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give 338 mg of the title compound as a colorless oil.

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-324ea0d4d6284a639e469e27d7f5dfc8
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618094B2

Reaction notes

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