Methyl benzilate → 1-Benzyl-3-pyrrolidinyl hydroxy(diphenyl)acetate

HRID 1706702

Reaction equation

HRID 1706702 reaction equation
[C:1]([O:17][CH3:18])(=[O:16])[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH2:19]([N:26]1[CH2:30]C[CH:28](O)[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCCCCCC.[H-].[Na+]>[CH2:19]([N:26]1[CH2:27][CH2:28][CH:18]([O:17][C:1](=[O:16])[C:2]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[OH:3])[CH2:30]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 66159Methyl benzilateHCID 69889N-benzyl-3-pyrrolidinol

Product 1

HCID 3800231-Benzyl-3-pyrrolidinyl hydroxy(diphenyl)acetateYield 101.5%

Reagents, catalysts & solvents 2

HCID 24758Sodium hydrideCatalystHCID 8900HeptaneSolvent

Procedure

To a solution of 12 g methyl benzilate and 8.2 g 1-benzyl-3-pyrrolidinol in 200 ml n-heptane is added 100 mg sodium hydride and the mixture refluxed for 4 hours, separating the methanol formed in a Dean-Stark separator. The cooled organic phase is washed with water and then extracted with 2N HCl. The aqueous phase is made alkaline with solid K2CO3 and extracted with ether to give 1-benzyl-3-(2,2-diphenyl-2-hydroxyacetoxy)pyrrolidine as an oil (18.2 g).

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. customseparating the methanol
  3. customformed in a Dean-Stark separator
  4. washThe cooled organic phase is washed with water
  5. extractionextracted with 2N HCl
  6. extractionextracted with ether

Sources & evidence

ORD record
ord-494760050aa44a46aff9a0798b0e60de
Source dataset
uspto-grants-1980_06
Patent number
US04208423

Linked notes

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