Methanol → (2S,4S)-4-methoxypyrrolidine-2-carboxylic acid

HRID 1447445Notes

Reaction equation

HRID 1447445 reaction equation
C([N:11]1[CH2:18][C@@H:17]([O:19][CH3:20])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.CO.[H][H]>[Pd].O>[CH3:20][O:19][C@@H:17]1[CH2:18][NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16]1

Participants

6

Reactant 3

HCID 887MethanolHCID 12849520(2S,4S)-1-[(Benzyloxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 12849452(2S,4S)-4-methoxypyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 6.8 g. of N-carbobenzyloxy-cis-4-methoxy-L-proline, 210 ml. of 2:1 methanol and water, and 2.3 g. of 5% Pd-C is placed on a hydrogenator at 3 atmospheres of hydrogen for four hours. The mixture is filtered to remove the catalyst and the filtrate evaporated to give 3.15 g. of a grayish solid; m.p. 218°-220° (dec.). A sample is crystallized from methanol-ether to yield colorless cis-4-methoxy-L-proline, m.p. 224°-226° (dec.), [α]D25 -42° (c, 1% in methanol).

Workup

  1. additionA mixture of 6.8 g
  2. filtrationThe mixture is filtered
  3. customto remove the catalyst
  4. customthe filtrate evaporated
  5. customto give 3.15 g
  6. customA sample is crystallized from methanol-ether

Sources & evidence

ORD record
ord-83892ec46f9b408fad47ca79b20e9de8
Source dataset
uspto-grants-1982_02
Patent number
US04316906

Reaction notes

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