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

HRID 1706702

반응식

HRID 1706702 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24758Sodium hydride촉매HCID 8900Heptane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-494760050aa44a46aff9a0798b0e60de
출처 데이터셋
uspto-grants-1980_06
특허 번호
US04208423

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