Propylene Oxide → Cis-4-Hydroxy-D-Proline

HRID 1976229Notes

Reaction equation

HRID 1976229 reaction equation
Cl.[OH:2][C@H:3]1[CH2:7][NH:6][C@@H:5]([C:8]([OH:10])=[O:9])[CH2:4]1.C1OC1C>C(O)C>[OH:2][C@H:3]1[CH2:7][NH:6][C@@H:5]([C:8]([OH:10])=[O:9])[CH2:4]1

Participants

4

Reactant 2

HCID 6378Propylene OxideHCID 12310682cis-4-Hydroxy-D-proline hydrochloride

Product 1

HCID 440014Cis-4-Hydroxy-D-ProlineYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4.5 g of cis-4-hydroxy-D-proline hydrochloride in 300 ml of ethanol, there was added 13.1 g of propylene oxide at room temperature and then the mixture was heated under refluxing for one hour. After allowing the reaction liquid to cool, the crystals precipitated were filtered off, washed with ethanol and then dried to give 3.0 g (yield 85.4%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder refluxing for one hour
  3. customthe reaction liquid
  4. temperatureto cool
  5. customthe crystals precipitated
  6. filtrationwere filtered off
  7. washwashed with ethanol
  8. customdried

Sources & evidence

ORD record
ord-3f26763b80a24a19a92ac78a613c5999
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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