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

HRID 732349Notes

Reaction equation

HRID 732349 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.[CH3:14]O>>[ClH:3].[CH3:14][O:12][C:11]([C@H:8]1[CH2:7][C@@H:6]([OH:5])[CH2:10][NH:9]1)=[O:13]

Participants

4

Reactant 3

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

Product 1

HCID 12764090Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochlorideYield 82%

Procedure

Add thionyl chloride (5.5 mL, 75.8 mmol) to an ice-cold suspension of 4-(R)-hydroxypyrrolidine-2-(R)-carboxylic acid (4.97 g, 31.9 mmol) in methanol (60 mL). Stir 10 min, then warm to room temperature and stir 3.5 h. Concentrate, add methanol, and concentrate again. Dissolve in absolute ethanol (25 mL) and precipitate with diethyl ether (50 mL) and filter. Dry cake under vacuum to give the title compound as a white solid (4.77 g, 82%).

Workup

  1. stirringstir 3.5 h
  2. concentrationConcentrate
  3. additionadd methanol
  4. concentrationconcentrate again
  5. dissolutionDissolve in absolute ethanol (25 mL)
  6. customprecipitate with diethyl ether (50 mL)
  7. filtrationfilter
  8. customDry cake under vacuum

Sources & evidence

ORD record
ord-ca476a49923b4c1c88f3da697bd0a4b9
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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