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

HRID 1279648
Notes
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Reaction equation

HRID 1279648 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 18427804Ethyl 3-[1-benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]-4-nitrobutanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 184278204-[1-Benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]-2-pyrrolidoneYield 70.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702
Ethanol
Solvent

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

  1. temperatureAfter cooling in an ice bath
  2. filtrationthe reaction solution was filtered through celite
  3. customthe solvent was evaporated under a reduced pressure
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes