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

HRID 1934835Notes

Reaction equation

HRID 1934835 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].[CH3:14][O:8][C:7](=[O:9])[C@H:4]1[CH2:3][C@@H:2]([OH:1])[CH2:6][NH:5]1

Participants

4

Reactant 3

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

Product 1

HCID 12764090Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

Conditions

Temperature
0 °C

Procedure

A suspension of 65.0 g (0.50 mol) of cis-4-hydroxy-D-proline in 1500 mL of methanol was cooled to 0° C. and 110 mL (179 g, 1.5 mol) of thionyl chloride was added dropwise at 0-5° C. The mixture was then allowed to warm to room temperature overnight. The volatiles were removed under reduced pressure and the residue was triturated with diethyl ether to afford 98.73 g of crude cis-4-hydroxy-D-proline methyl ester hydrochloride as a white solid.

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-7d65212ca3b54634bbd4a2f5f9a35569
Source dataset
uspto-grants-2002_05
Patent number
US06384234B1

Reaction notes

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