Triethylamine → (S)-1-(4-chlorophenethyl)-3-methanesulfonyloxypyrrolidine

HRID 1859465Notes

Reaction equation

HRID 1859465 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH2:7][N:8]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl.O>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH2:7][N:8]2[CH2:12][CH2:11][C@H:10]([O:13][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69899443(S)-1-(4-chlorophenethyl)-3-hydroxypyrrolidine

Product 1

HCID 86585525(S)-1-(4-chlorophenethyl)-3-methanesulfonyloxypyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

(S)-1-(4-Chlorophenethyl)-3-hydroxypyrrolidine (190 mg, 0.84 mmol) was dissolved in dichloromethane (6 ml). Triethylamine (110 mg, 1.09 mmol) and methanesulfonyl chloride (125 mg, 1.09 mmol) were added to the obtained solution under stirring under cooling on ice. They were stirred at 0° C. for 1 hour. The reaction liquid was distributed in dichloromethane and water. The organic layer was dried, and the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with dichloromethane and then with a solvent mixture of dichloromethane and methanol (50:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (S)-1-(4-chlorophenethyl)-3-methanesulfonyloxypyrrolidine in the form of a light yellow oil (252 mg, 99%).

Workup

  1. temperatureunder cooling on ice
  2. stirringThey were stirred at 0° C. for 1 hour
  3. customThe reaction liquid
  4. customThe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure
  6. washThe product was eluted with dichloromethane
  7. additionwith a solvent mixture of dichloromethane and methanol (50:1)
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f8ea3d41a31a4d8b898334ec49aa4e2b
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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