tert.-Butyl N-(cis-1-benzyl-4-methoxypyrrolidin-3-yl)-carbamate → cis-3-(Boc-amino)-4-methoxypyrrolidine

HRID 981073Notes

Reaction equation

HRID 981073 reaction equation
C([N:8]1[CH2:12][C@H:11]([O:13][CH3:14])[C@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH3:14][O:13][C@H:11]1[CH2:12][NH:8][CH2:9][C@H:10]1[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21]

Participants

4

Reactant 1

HCID 86744570tert.-Butyl N-(cis-1-benzyl-4-methoxypyrrolidin-3-yl)-carbamate

Product 1

HCID 86744571cis-3-(Boc-amino)-4-methoxypyrrolidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.5 g (11.4 mmol) of tert.-butyl N-(cis-1-benzyl-4-methoxypyrrolidin-3-yl)-carbamate are hydrogenated in 100 ml of methanol on 2 g of palladium-on-active charcoal (10% of Pd) at 100° C. under 100 bar. The catalyst is filtered off, the filtrate is concentrated and the residue is distilled.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. distillationthe residue is distilled

Sources & evidence

ORD record
ord-2912c0404adf488782f3482e5074560e
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

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