Triethylamine → HCID 59644029, compound

HRID 1859461Notes

Reaction equation

HRID 1859461 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]3[O:15][CH2:16][O:17][C:11]=3[CH:10]=2)[CH2:3]1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl.O>[CH3:25][S:26]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]3[O:15][CH2:16][O:17][C:11]=3[CH:10]=2)[CH2:3]1)(=[O:28])=[O:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69900710HCID 69900710, compound

Product 1

HCID 59644029HCID 59644029, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

(S)-3-Hydroxy-1-(3,4-methylenedioxyphenethyl)pyrrolidine (281 mg, 1.19 mmol) was dissolved in dichloromethane (8 ml). Triethylamine (162 mg, 1.60 mmol) and methanesulfonyl chloride (183 mg, 1.60 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)-3-methanesulfonyloxy-1-(3,4-methylenedioxyphenethyl) pyrrolidine in the form of a light yellow oil (359 mg, 97%).

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-e38d2024e5794c3a9c12e035750fec48
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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