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

HRID 36652Notes

Reaction equation

HRID 36652 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-e7fca8ab410b4da2b101d9eab7ecb9cc
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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