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

HRID 1279662Notes

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](OCC)=[O:24])([C:13]([O:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[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:24])[CH2:22]2)([C:13]([O:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A 11.45 g (25.26 mmol) portion of crude ethyl 3-[1-benzyloxy-3-(isoamyloxycarbonyl)cyclobutan-3-yl]-4-nitrobutanoate was dissolved in 200 ml of ethanol to which was subsequently added 10 ml of Raney nickel under an atmosphere of nitrogen. After replacing nitrogen with hydrogen, this was stirred at 50° C. for 5 hours under an atmosphere of hydrogen. After cooling in an ice bath, the reaction solution was filtered through celite and then the solvent was evaporated under a reduced pressure to give 6.51 g (19.5 mmol) of the title compound. The thus obtained compound was used in the following reaction without purification.

Workup

temperatureAfter cooling in an ice bath
filtrationthe reaction solution was filtered through celite
customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record: ord-2de2fe1682a446bda0105d8fc41ec897
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448266B1

Reaction notes

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