Benzoyl chloride → 2-Pyrrolidinemethanol, 1-benzoyl-, (2S)-

HRID 248885Notes

Reaction equation

HRID 248885 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[CH2:21][OH:22]>CC(C)=O.O>[C:1]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[CH2:21][OH:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 640091L-Prolinol

Product 1

HCID 128307942-Pyrrolidinemethanol, 1-benzoyl-, (2S)-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Benzoyl chloride (18.5 ml) and an aqueous (50 ml) solution of sodium carbonate (17.0 g) were added dropwise to a solution of (S)-2pyrrolidinemethanol (12.0 g) in a mixture of acetone (70 ml) and water (14 ml). After addition, the reaction mixture was stirred for 30 mins at room temperature. The reaction mixture was filtered. Water was added to the filtrate. The mixture was extracted with methylene chloride. The extract was washed, dried and evaporated. The residue was purified by column chromatography on silica-gel (hexane-EtOAc) to give the title compound (24.1 g) having the following physical data:

Workup

  1. additionAfter addition
  2. filtrationThe reaction mixture was filtered
  3. additionWater was added to the filtrate
  4. extractionThe mixture was extracted with methylene chloride
  5. washThe extract was washed
  6. customdried
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica-gel (hexane-EtOAc)

Sources & evidence

ORD record
ord-2db4233cd7f841028f78115a5700eaf1
Source dataset
uspto-grants-1993_05
Patent number
US05212191

Reaction notes

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