1,1-Dimethylethyl N-[[3-hydroxy-1-(phenylmethyl)-3-pyrrolidinyl]methyl]carbamate → 3-(Boc-aMinoMethyl)-3-hydroxypyrrolidine

HRID 2400082Notes

Reaction equation

HRID 2400082 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([OH:13])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[C:19]([O:18][C:16]([NH:15][CH2:14][C:10]1([OH:13])[CH2:11][CH2:12][NH:8][CH2:9]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 1

HCID 544893721,1-Dimethylethyl N-[[3-hydroxy-1-(phenylmethyl)-3-pyrrolidinyl]methyl]carbamate

Product 1

HCID 537161023-(Boc-aMinoMethyl)-3-hydroxypyrrolidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

18.7 g (61 mmol) of 1-benzyl-3-tert.-butoxycarbonylaminomethyl-3-hydroxypyrrolidine are dissolved in 120 ml of methanol and hydrogenated on 3 g of 5% strength Pd/active carbon at 90° C. and 100 bar. The catalyst is filtered off, the filtrate is concentrated and the residue is recrystallized from ethyl acetate.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-792d1892bf3d4eee9a0d09dcacf84906
Source dataset
uspto-grants-1995_09
Patent number
US05453422

Reaction notes

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