Methanol → Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

HRID 1941600Notes

Reaction equation

HRID 1941600 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[OH:1][C@H:2]1[CH2:6][NH:5][C@@H:4]([C:7]([O:9][CH3:14])=[O:8])[CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 440014Cis-4-Hydroxy-D-Proline

Product 1

HCID 12764090Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochlorideYield 113%

Procedure

To a suspension of cis-4-hydroxy-D-proline (16.46 g: 125.5 mmole) in methanol (66 ml), thionylchloride (9.16 ml: 125.5 mmole) is added in a nitrogen atmosphere under ice cooling, and the mixture is stirred at room temperature for 30 minutes. The mixture is further stirred to react at 40° C. for 4 hours to give (2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride as crude crystals (25.74 g). Yield: 113%. Colorless crystals.

Workup

  1. additionis added in a nitrogen atmosphere under ice cooling
  2. stirringThe mixture is further stirred
  3. customto react at 40° C. for 4 hours

Sources & evidence

ORD record
ord-14a8ce6d2fba4752b0817baa0f370deb
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

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