Methanol → (4R)-4-Hydroxy-L-proline methyl ester

HRID 2203123Notes

Reaction equation

HRID 2203123 reaction equation
S(Cl)(Cl)=O.[OH:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1.[CH3:14]O>>[CH3:14][O:12][C:11]([C@@H:8]1[CH2:7][C@@H:6]([OH:5])[CH2:10][NH:9]1)=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 5810L-HydroxyprolineHCID 24386Thionyl Chloride

Product 1

HCID 7015125(4R)-4-Hydroxy-L-proline methyl ester

Procedure

Thionyl chloride (47 g, 393 mmol) was added dropwise at 0° C. to a stirred solution of (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid (40 g, 0.31 mol) in anhydrous methanol (200 mL). The reaction was allowed to proceed overnight, and concentrated to give the title intermediate (50 g). 1H NMR (400 MHz, CD3OD) δ (ppm) 4.56 (m, 2H), 3.85 (s, 3H), 3.41 (m, 1H), 3.28 (m, 1H), 2.40 (m, 1H), 2.22 (m, 1H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-7d7dcce286bf4f96b2dfe07999801660
Source dataset
uspto-grants-2016_06
Patent number
US09365549B2

Reaction notes

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