proline dl-form → Methyl DL-prolinate

HRID 1397070Notes

Reaction equation

HRID 1397070 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>>[CH3:13][O:11][C:10]([CH:6]1[CH2:7][CH2:8][CH2:9][NH:5]1)=[O:12]

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 methylpyrrolidine-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-91613375dc8a4ec5afb336a08b57a1fb
Source dataset
uspto-grants-2014_12
Patent number
US08901140B2

Reaction notes

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