Methanol → (2R,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate

HRID 81392

Reaction equation

HRID 81392 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.[CH3:14]O>>[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 7020012(2R,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate

Conditions

Temperature
0 °C

Procedure

7.1 30 g of (2R,4R)-4-hydroxy pyrrolidine-2-carboxylic acid are suspended in 200 ml of methanol and cooled to 0° C. Thionyl chloride (18.1 ml) is subsequently added dropwise at the same temperature distributed over an hour. The reaction mixture (RM) is warmed to room temperature (RT) over 12 h, during which a clear solution forms. The solvent is removed in vacuo, and the residue obtained is recrystallised from ether, giving 50 g of methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate; Rt.: 0.386 min; [M+H]+146.2.

Workup

  1. waitdistributed over an hour
  2. temperatureThe reaction mixture (RM) is warmed to room temperature (RT) over 12 h
  3. customThe solvent is removed in vacuo
  4. customthe residue obtained
  5. customis recrystallised from ether

Sources & evidence

ORD record
ord-c8cd2170bd6c4e7e91f7981f70c83f6d
Source dataset
uspto-grants-2014_09
Patent number
US08846694B2

Linked notes

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