Ethyl 3-[1-benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]-4-nitrobutanoate → 4-[1-Benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]-2-pyrrolidone

HRID 1279648Notes

Reaction equation

[CH2:1]([O:8][CH:9]1[CH2:12][C:11]([CH:21]([CH2:28][N+:29]([O-])=O)[CH2:22][C:23]([O:25]CC)=O)([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Ni]>[CH2:1]([O:8][CH:9]1[CH2:12][C:11]([CH:21]2[CH2:28][NH:29][C:23](=[O:25])[CH2:22]2)([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A 35.12 g (80.46 mmol) portion of ethyl 3-[1-benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]-4-nitrobutanoate was dissolved in 700 ml of ethanol to which, under an atmosphere of nitrogen, was subsequently added 50 ml of Raney nickel. After replacing the atmosphere with hydrogen, this was stirred at 50° C. for 5 hours. After cooling in an ice bath, the reaction solution was filtered through celite and then the solvent was evaporated under a reduced pressure. Thereafter, the resulting residue was purified by a silica gel column chromatography to give 20.53 g (70.8%) of the title compound.

Workup

temperatureAfter cooling in an ice bath
filtrationthe reaction solution was filtered through celite
customthe solvent was evaporated under a reduced pressure
customThereafter, the resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record: ord-60937e23189a4efe8aee17bb42611346
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448266B1

Reaction notes

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