tert.-Butyl N-(trans-1-benzyl-4-methoxypyrrolidin-3yl)carbamate → rac-tert-butyl N-[(3R,4R)-4-methoxypyrrolidin-3-yl]carbamate

HRID 36654Notes

Reaction equation

HRID 36654 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 15069969tert.-Butyl N-(trans-1-benzyl-4-methoxypyrrolidin-3yl)carbamate

Product 1

HCID 15069971rac-tert-butyl N-[(3R,4R)-4-methoxypyrrolidin-3-yl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6.7 g (22 mmol) of tert.-butyl N-(trans-1-benzyl-4-methoxypyrrolidin-3-yl)carbamate are hydrogenated in 150 ml of methanol on 2 g of palladium-on-active charcoal (10% of Pd) under 100 bar at 100° C. The catalyst is filtered off with suction, the filtrate is concentrated and the residue is distilled.

Workup

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

Sources & evidence

ORD record
ord-94462c4fdb6a43548a178c056ea9d5a2
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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