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1-Benzyl-cis-3-t-butoxycarbonylamino-4-methylpyrrolidine → (3S,4S)-3-(Boc-amino)-4-methylpyrrolidine

HRID 580563
Notes
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Reaction equation

HRID 580563 reaction equation
C([N:8]1[CH2:12][C@H:11]([CH3:13])[C@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:18]([O:17][C:15]([NH:14][C@H:10]1[C@@H:11]([CH3:13])[CH2:12][NH:8][CH2:9]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 108808031-Benzyl-cis-3-t-butoxycarbonylamino-4-methylpyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 11138119(3S,4S)-3-(Boc-amino)-4-methylpyrrolidineYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-benzyl-cis-3-t-butoxycarbonylamino-4-methylpyrrolidine (5.37 g) and 10% palladium-on-charcoal (2.70 g) in ethanol (50 ml) was shaken with hydrogen were absorbed under elevated pressure (100 kg/cm2) at room temperature for 22 hours. The catalyst was removed by filtration and the filtrate was evaporated to give the title compound (3.25 g). The compound was gradually solidified at room temperature.

Workup

  1. customwere absorbed under elevated pressure (100 kg/cm2) at room temperature for 22 hours
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-6fa11b429bad4daea129c07ad2314b43
Source dataset
uspto-grants-1988_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04753953

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes