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HCID 70202469, compound → rac-tert-butyl N-[(3R,4S)-4-methylpyrrolidin-3-yl]carbamate

HRID 580566
Notes
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Reaction equation

HRID 580566 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 70202469HCID 70202469, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53686699rac-tert-butyl N-[(3R,4S)-4-methylpyrrolidin-3-yl]carbamateYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-benzyl-trans-3-t-butoxycarbonylamino-4-methylpyrrolidine (4.8 g) and 10% palladium-on-charcoal (1.8 g) in ethanol (40 ml) was shaken with hydrogen were absorbed under elevated pressure (100 kg/cm2) at 50°-70° C. for 6.5 hours. The catalyst was removed by filtration and the filtrate was evaporated to give the title compound (3.09 g) as brown oil. This oil was gradually solidified at room temperature.

Workup

  1. customwere absorbed under elevated pressure (100 kg/cm2) at 50°-70° C. for 6.5 hours
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-cba856acedb249e185beebb58b31f2d8
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