Water → (2R)-2-Cyclopentyl-2-hydroxy-2-phenylacetic acid 1-ethylpyrrolidin-3-yl ester

HRID 458897노트

반응식

HRID 458897 반응식
[CH:1]1([C@@:6]([OH:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]([N:19]1[CH2:23][CH2:22][CH:21](O)[CH2:20]1)[CH3:18].O>CN(C=O)C>[CH2:17]([N:19]1[CH2:23][CH2:22][CH:21]([O:8][C:7](=[O:9])[C@:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)([OH:16])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:20]1)[CH3:18]

참가 물질

5

반응물 3

HCID 962WaterHCID 982031-Ethyl-3-pyrrolidinolHCID 948620alpha-Cyclopentylmandelic acid, (+)-

생성물 1

HCID 69481435(2R)-2-Cyclopentyl-2-hydroxy-2-phenylacetic acid 1-ethylpyrrolidin-3-yl ester수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

0.655 g (0.00297 mol) of (2R)-2-Cyclopentyl-2-hydroxy-2-phenylacetic acid were dissolved in 8 ml of dry DMF. To this solution 0.580 g (0.0036 mol) of 1,1′-carbonildiimidazol were added and the mixture was stirred at room temperature for 1 h. After this time, the mixture obtained was added to a suspension (cooled at 0° C.) of 1-ethylpyrrolidin-3-ol (0.390 ml g, 0.0033 mol) and HNa (0.078 g, 0.0033 mol) in 4 ml of dry DMF. After stirring 15 h at room temperature the reaction mixture was treated with water and extracted three times with Et2O. The organic layers were combined, washed with water and dried. The residue was purified by silica gel column chromatography (eluent: CHCl3 plus isopropanol 0%→5%) to obtain 610 mg (65%) of the title product as an oil.

후처리

  1. customAfter this time, the mixture obtained
  2. stirringAfter stirring 15 h at room temperature the reaction mixture
  3. extractionextracted three times with Et2O
  4. washwashed with water
  5. customdried
  6. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 plus isopropanol 0%→5%)

출처 및 근거

ORD 기록
ord-9b5f7d1db6184f36aa6c8043603753a3
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192978B2

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