Benzyl chloroformate → [(1S,5S)-3-Benzyloxycarbonyl-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester

HRID 1917364Notes

Reaction equation

[C:1]([O:5][C:6]([C@@:8]12[CH:15]=[CH:14][CH2:13][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].[CH2:24]([O:31][C:32](Cl)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClC(Cl)C>[C:1]([O:5][C:6]([C@@:8]12[CH:15]=[CH:14][CH2:13][C@@H:12]1[CH2:11][N:10]([C:32]([O:31][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:33])[CH2:9]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

[(1S,5S)-3-[(1R)-1-Phenylethyl]-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester (370 mg, 1.18 mmol) was dissolved in dichloroethane (3 mL). Benzyloxycarbonyl chloride (1.01 g, 5.90 mmol) was added, and the mixture was stirred at 40° C. for three hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (10% ethyl acetate/hexane) to give 385 mg of the title compound as a colorless oil.

Workup

concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-129a72ee8a2a400dbdf71a1171493c78
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618094B2

Reaction notes

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