Acetyl chloride → (3S)-1-benzyl-3-acetoxypyrrolidine

HRID 15082

Reaction equation

HRID 15082 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].C1COCC1.[CH2:17]([N:24]1[CH2:28][CH2:27][C@H:26]([OH:29])[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)(=O)C>[CH2:17]([N:24]1[CH2:28][CH2:27][C@H:26]([O:29][C:8](=[O:10])[CH3:9])[CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 15623663(3S)-1-benzyl-3-acetoxypyrrolidineYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (1.3 mL, 9.30 mmols) and acetyl chloride (0.6 mL, 8.46) were added to THF (20 mL) solution of (3S)-1-benzyl-3-hydroxypyrrolidine (1.5 g, 8.46 mmols) by the order stated, under cooling with ice, and stirred at the same temperature for an hour. Ethyl acetate was added to the reaction liquid which then was washed with water and saturated brine, and dried over anhydrous sodium sulfate. Concentrating the reaction liquid under reduced pressure, the residue was purified on silica gel column chromatography (KP—NH, ethyl acetate:hexane=1:20) to provide the title compound (1.68 g, 90%).

Workup

  1. temperatureunder cooling with ice
  2. washthen was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationConcentrating
  5. customthe reaction liquid under reduced pressure
  6. customthe residue was purified on silica gel column chromatography (KP—NH, ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-08c55e9d266e442688fef7b33c0e6450
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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