N-benzyl-3-benzoyloxypyrrolidine → (S)-(-)-3-benzoyloxypyrrolidine

HRID 1966087Notes

Reaction equation

HRID 1966087 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCl.CO>[C:14]([O:13][C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 223922N-benzyl-3-benzoyloxypyrrolidineHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 11160511(S)-(-)-3-benzoyloxypyrrolidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a crude mixture of N-benzyl-3-benzoyloxypyrrolidine (114 mg, 0.41 mmol) in dichloromethane (1 mL) is added α-chloroethyl chloroformate (57 μL, 0.49 mmol) at 0° C., and the mixture is stirred for 1 hour while warming to room temperature. After removing dichloromethane, resulting mixture is diluted with MeOH. The reaction mixture is heated to 80° C. for 0.5 hour. After cooling to room temperature, solvent is evaporated under reduced pressure to obtain (S)-(−)-3-benzoyloxypyrrolidine which is used for next reaction without further purification.

Workup

  1. customAfter removing dichloromethane
  2. customresulting mixture
  3. temperatureThe reaction mixture is heated to 80° C. for 0.5 hour
  4. temperatureAfter cooling to room temperature
  5. customsolvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-7da3821c1a314880afce32478465ec1a
Source dataset
uspto-grants-2013_04
Patent number
US08420641B2

Reaction notes

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