benzyl (2S,4R)-2-(hydroxymethyl)-4-methoxypyrrolidine-1-carboxylate → ((2S,4R)-4-methoxypyrrolidin-2-yl)methanol

HRID 2308095Notes

Reaction equation

HRID 2308095 reaction equation
C(OC([N:11]1[CH2:15][C@H:14]([O:16][CH3:17])[CH2:13][C@H:12]1[CH2:18][OH:19])=O)C1C=CC=CC=1>CO>[CH3:17][O:16][C@H:14]1[CH2:15][NH:11][C@H:12]([CH2:18][OH:19])[CH2:13]1

Participants

3

Reactant 1

HCID 59971156benzyl (2S,4R)-2-(hydroxymethyl)-4-methoxypyrrolidine-1-carboxylate

Product 1

HCID 55299876((2S,4R)-4-methoxypyrrolidin-2-yl)methanolYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1.00 g (5.62 mmol) of (2S,4R)-2-Hydroxymethyl-4-methoxy-pyrrolidine-1-carboxylic acid benzyl ester in 3 mL of MeOH was added 0.1 g of 10% Pd(C) under 1 atmosphere of H2 while stirring for 12 h. The mixture was filtered through 0.22 μM Teflon filter concentrated and put under high vacuum for 2 h to give 0.44 g (96%) of ((2S,4R)-4-Methoxy-pyrrolidin-2-yl)-methanol as clear oil. LCMS (APCI) (M+H+) m/z: 266.2.

Workup

  1. filtrationThe mixture was filtered through 0.22 μM Teflon
  2. filtrationfilter
  3. concentrationconcentrated
  4. waitput under high vacuum for 2 h

Sources & evidence

ORD record
ord-cc5ce8e680d24746ba69825aabfbc9c3
Source dataset
uspto-grants-2004_12
Patent number
US06833456B2

Reaction notes

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