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

HRID 2176444Notes

Reaction equation

HRID 2176444 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-d68c59e1b6b34bf48bf47b1869bbee64
Source dataset
uspto-grants-2015_06
Patent number
US09066944B2

Reaction notes

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