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

HRID 1974879Notes

Reaction equation

HRID 1974879 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-5d21f7c4e10b45aea8b2dabea91dc9de
Source dataset
uspto-grants-1994_02
Patent number
US05284842

Reaction notes

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