Ethanol → Ethyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

HRID 2304401Notes

Reaction equation

HRID 2304401 reaction equation
S(Cl)([Cl:3])=O.[OH:5][C@H:6]1[CH2:10][NH:9][C@@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1.[CH2:14](O)[CH3:15]>>[ClH:3].[CH2:14]([O:12][C:11]([C@H:8]1[CH2:7][C@@H:6]([OH:5])[CH2:10][NH:9]1)=[O:13])[CH3:15]

Participants

4

Reactant 3

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

Product 1

HCID 12709308Ethyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

Procedure

3.27 g(27.5 mmol) of thionyl chloride was added dropwise to a suspension of cis-4-hydroxy-D-proline (3.00 g, 2.9 mmol) in ethanol (15 ml) and the mixture was refluxed for 2 hours. The mixture was concentrated, acetone was added to the residue and the solution was cooled on ice. The resultant precipitate was filtered and 4.23 g of (2R, 4R)-(+)-2-(ethoxycarbonyl)-4-hydroxypyrrolidine hydrochloride was obtained as colorless needles (94.5%).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. concentrationThe mixture was concentrated
  3. additionacetone was added to the residue
  4. temperaturethe solution was cooled on ice
  5. filtrationThe resultant precipitate was filtered

Sources & evidence

ORD record
ord-1718dbe1c89d430c80b23c90e26d7579
Source dataset
uspto-grants-2002_08
Patent number
US06436922B1

Reaction notes

Loading…