Ethanol → (2R,4R)-ethyl 4-hydroxypyrrolidine-2-carboxylate

HRID 906215

Reaction equation

HRID 906215 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)=O.[CH2:14](O)[CH3:15]>>[CH2:14]([O:8][C:7]([C@H:4]1[CH2:3][C@@H:2]([OH:1])[CH2:6][NH:5]1)=[O:9])[CH3:15]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 440014Cis-4-Hydroxy-D-Proline

Product 1

HCID 6992702(2R,4R)-ethyl 4-hydroxypyrrolidine-2-carboxylate

Procedure

To a stirred solution of cis-4-hydroxy-pyrrolidine-2-carboxylic acid (1 g, 7.6 mmol) in absolute ethanol (20 mL) is added dropwise thionyl chloride (0.67 mL, 9.15 mmol) at 0° C. under nitrogen atmosphere. The reaction mixture is then refluxed under nitrogen for about 2 h. The mixture is cooled to room temperature, and all solvent is removed under reduced pressure. The white precipitate is filtered and washed with diethyl ether (1×25 mL), to obtain compound (1) as a white solid.

Workup

  1. temperatureThe reaction mixture is then refluxed under nitrogen for about 2 h
  2. customall solvent is removed under reduced pressure
  3. filtrationThe white precipitate is filtered
  4. washwashed with diethyl ether (1×25 mL)

Sources & evidence

ORD record
ord-98e4c14cff344515843593c5d1a72215
Source dataset
uspto-grants-2011_09
Patent number
US08012983B2

Linked notes

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