Triethylamine → (S)-1-(4-dimethylaminophenethyl)-3-methanesulfonyloxy-pyrrolidine

HRID 1859452Notes

Reaction equation

HRID 1859452 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:16]=[CH:15][C:6]([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl.O>[CH3:17][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([O:14][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:10]2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69900648(S)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine

Product 1

HCID 86585524(S)-1-(4-dimethylaminophenethyl)-3-methanesulfonyloxy-pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

(S)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine (320 mg, 1.37 mmol) was dissolved in dichloromethane (10 ml). Triethylamine (152 mg, 1.50 mmol) and methanesulfonyl chloride (164 mg, 1.43 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 (50:1) of dichloromethane and methanol. The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (S)-1-(4-dimethylaminophenethyl)-3-methanesulfonyloxy-pyrrolidine in the form of a light yellow oil (378 mg, 88%).

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
  6. washThe product was eluted with dichloromethane
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a6aea6b868d242b8895442c66ea8c458
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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