Methanol → 2-Methyl-L-proline Methyl ester hydrochloride

HRID 496231Notes

Reaction equation

HRID 496231 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C@@:6]1([C:11]([OH:13])=[O:12])[CH2:10][CH2:9][CH2:8][NH:7]1.[CH3:14]O>>[ClH:3].[CH3:5][C@@:6]1([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9][CH2:8][NH:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 69936642-Methyl-L-proline

Product 1

HCID 575164552-Methyl-L-proline Methyl ester hydrochloride

Conditions

Temperature
0 °C

Procedure

To a solution of anhydrous MeOH (65 mL) at 0° C. was added thionyl chloride (9.03 mL, 124 mmol) slowly over a 5 min period. 2-Methyl-(L)-proline (Bachem AG, Cat. No. F-3440, Bubendorf, Switzerland) (4.0 gm, 31 mmol) was added in one portion. The reaction was stirred at 0° C. for 5 min and then warmed to rt. The reaction was then heated to 70° C. overnight. The reaction was cooled and the solvent removed to yield 2-methyl-(L)-proline, methyl ester hydrochloride as a white solid (5.72 gm).

Workup

  1. additionF-3440, Bubendorf, Switzerland) (4.0 gm, 31 mmol) was added in one portion
  2. temperaturewarmed to rt
  3. temperatureThe reaction was then heated to 70° C. overnight
  4. temperatureThe reaction was cooled
  5. customthe solvent removed

Sources & evidence

ORD record
ord-b144ab72bd8b40a5916f30af8c450795
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

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