proline dl-form → Methyl DL-prolinate

HRID 2199354Notes

Reaction equation

HRID 2199354 reaction equation
S(Cl)(Cl)=O.[NH:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]([OH:12])=[O:11].[CH3:13]O>>[NH:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 3

HCID 614proline dl-formHCID 887MethanolHCID 24386Thionyl Chloride

Product 1

HCID 94239Methyl DL-prolinate

Procedure

7 mL of thionyl chloride was dissolved in 50 mL of methanol in an ice-water bath, followed by addition of pyrrolidine-2-carboxylic acid 10a (5 g, 43.40 mmol). The mixture was warmed up to room temperature and stirred for 24 hours. The mixture was concentrated under reduced pressure to obtain methyl pyrrolidine-2-carboxylate 10b (10 g) crude product as a white solid, which was directly used in the next step without purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-78b300fcbaa34da1877428fe4d6febbf
Source dataset
uspto-grants-2016_06
Patent number
US09358227B2

Reaction notes

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