Triethylamine → (S)-3-methanesulfonyloxy-1-(4-methoxyphenethyl)pyrrolidine
Reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH2:3]1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl.O>[CH3:24][S:25]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[CH2:3]1)(=[O:27])=[O:26]Participants
Procedure
(S)-3-Hydroxy-1-(4-methoxyphenethyl)pyrrolidine (541 mg, 2.45 mmol) was dissolved in dichloromethane (15 ml). Triethylamine (272 mg, 2.69 mmol) and methanesulfonyl chloride (295 mg, 2.58 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 reduce 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)-3-methanesulfonyloxy-1-(4-methoxyphenethyl)pyrrolidine in the form of a white solid (734 mg, 100%).
Workup
- temperatureunder cooling on ice
- stirringThey were stirred at 0° C. for 1 hour
- customThe reaction liquid
- customThe organic layer was dried
- customthe solvent was evaporated
- washThe product was eluted with dichloromethane
- additionwith a solvent mixture of dichloromethane and methanol (50:1)
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-54bc0494b11a41cdafa7cdddfbc33338
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06528504B2
Reaction notes
Loading…