HCID 15623664, compound → N-benzyl-3-pyrrolidinol

HRID 2081947Notes

Reaction equation

HRID 2081947 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([O:13]C(=O)CCCCC)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P([O-])([O-])([O-])=O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 15623664HCID 15623664, compound

Product 1

HCID 69889N-benzyl-3-pyrrolidinol

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

First, 10 g of (RS)-N-benzyl-3-hexanoyloxypyrrolidine and one of the commercially available enzymes listed in Table 3 were added to 100 ml of 0.1 M phosphate buffer (pH 7.0). This mixture was allowed to react at 40° C. with agitation for 22-120 hours. Then, the unreacted (RS)-N-benzyl-3-hexanoyloxypyrrolidine was recovered by three extractions from the reaction mixture with equal volumes of hexane. The aqueous phase was then adjusted to pH 13 by the addition of NaOH, and the hydrolyzed N-benzyl-3-hydroxypyrrolidine was obtained by three extractions with equal volumes of hexane. After removal of the solvent under reduced pressure, distillation yielded purified N-benzyl-3-hydroxypyrrolidine in colorless, transparent, oily form. After tosylation, the optical purity of this purified product was measured by HPLC. The results with the different enzymes used are shown in Table 3.

Workup

  1. customto react at 40° C. with agitation for 22-120 hours
  2. customThen, the unreacted (RS)-N-benzyl-3-hexanoyloxypyrrolidine was recovered by three extractions from the reaction mixture with equal volumes of hexane
  3. additionThe aqueous phase was then adjusted to pH 13 by the addition of NaOH

Sources & evidence

ORD record
ord-ac378094c5b7462e9104163daf202ff0
Source dataset
uspto-grants-1993_02
Patent number
US05187094

Reaction notes

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