Benzyl Chloride → HCID 11470360, compound

HRID 975642Notes

Reaction equation

HRID 975642 reaction equation
Cl.[OH:2][C@H:3]1[CH2:7][NH:6][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4]1.C(N(CC)CC)C.[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[CH2:19]([N:6]1[CH2:7][C@H:3]([OH:2])[CH2:4][C@H:5]1[C:8]([O:10][CH3:11])=[O:9])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 114353194-Hydroxy-L-proline methyl ester hydrochloride

Product 1

HCID 11470360HCID 11470360, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylate hydrochloride (674 g) in dichloromethane (3.5 l) were added dropwise triethylamine (1.19 l) and benzyl chloride (552 ml) at 10°-20° C. under stirring and the mixture was refluxed for 6 hours. The mixture was cooled to ambient temperature, and the precipitates were removed by filtration. The filtrate was poured into 1N sodium hydroxide and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo to give methyl (2S,4R)-1-benzyl-4-hydroxy-2-pyrrolidinecarboxylate (663 g).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customthe precipitates were removed by filtration
  3. additionThe filtrate was poured into 1N sodium hydroxide
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6a3e30e2779a47abb6796ef36c053bb6
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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