Methanol → 4-Hydroxy-L-proline methyl ester hydrochloride

HRID 1011592Notes

Reaction equation

HRID 1011592 reaction equation
S(Cl)([Cl:3])=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>>[ClH:3].[OH:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 5810L-HydroxyprolineHCID 24386Thionyl Chloride

Product 1

HCID 114353194-Hydroxy-L-proline methyl ester hydrochlorideYield 95%

Procedure

Thionyl chloride (11.6 ml, 160 mmol) was added to a stirred solution of (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid (10.0 g, 76.26 mmol) (1) in methanol (150 ml) at −78° C. for 10 min. The mixture was then stirred in an ice bath for 30 minutes followed by stirring at RT for 30 min. Finally the mixture was refluxed for three hours and concentrated in vacuo to give (2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride (2) (17.90 g, 95%) as a white solid. Used without further purification. MS m/z 146.2 (M+H)+; retention time=0.19 min, method [1].

Workup

  1. stirringby stirring at RT for 30 min
  2. temperatureFinally the mixture was refluxed for three hours
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38a2a7004d324b9ca7d639cbca635c48
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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