Water → (R)-(R)-1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate

HRID 458896노트

반응식

HRID 458896 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.[CH3:17][N:18]1[CH2:22][CH2:21][C@@H:20](O)[CH2:19]1.O>CN(C=O)C>[CH3:17][N:18]1[CH2:22][CH2:21][C@@H:20]([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)[CH2:19]1

참가 물질

5

반응물 3

HCID 962WaterHCID 948620alpha-Cyclopentylmandelic acid, (+)-HCID 69513321-Methyl-3-pyrrolidinol, (-)-

생성물 1

HCID 6713896(R)-(R)-1-methylpyrrolidin-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate수율 60%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

0.545 g (0.0025 mol) of (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid were dissolved in 8 ml of dry DMF. To this solution 0.481 g (0.003 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 of (3R)-1-methylpyrrolidin-3-ol (Intermediate I-19, 0.531 g, 0.0046 mol) and HNa (0.065 g, 0.0027 mol) in 3 ml of dry DMF. After stirring 26 h at room temperature the reaction mixture was treated with water and extracted two 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%→10%) to obtain 450 mg (60%) of the title product as an oil.

후처리

  1. customAfter this time, the mixture obtained
  2. stirringAfter stirring 26 h at room temperature the reaction mixture
  3. extractionextracted two times with Et2O
  4. washwashed with water
  5. customdried
  6. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 plus isopropanol 0%→10%)

출처 및 근거

ORD 기록
ord-4b23e79910e64f2c9e8059d87618ae10
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192978B2

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