Water → 3-Hydroxy-5-methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one

HRID 1887495노트

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HRID 1887495 반응식
[CH2:1]=[C:2]1[CH2:22][CH:5]2[C:6](=[O:21])[N:7]([C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)[C:8](=[O:9])[CH:4]2[CH2:3]1.[BH4-].[Na+].O>CCO.ClCCl>[OH:9][CH:8]1[N:7]([C:10]2[CH:11]=[CH:12][C:13]([O:16][C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=2)[C:6](=[O:21])[CH:5]2[CH2:22][C:2](=[CH2:1])[CH2:3][CH:4]12

참가 물질

5

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 866739165-Methylene-2-(4-trifluoromethoxy-phenyl)-tetrahydro-cyclopenta[c]pyrrole-1,3-dione

생성물 1

HCID 866739173-Hydroxy-5-methylene-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one수율 78%

시약·촉매·용매 1

HCID 21584144Dichloromethane ethanol용매

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온도
-20 °C

실험 절차

To a cooled (−20° C.) solution of 5-Methylene-2-(4-trifluoromethoxy-phenyl)-tetrahydro-cyclopenta[c]pyrrole-1,3-dione (0.7 g, 2.25 mmol) in EtOH/dichloromethane (15/10 mL) were sequentially added CeCl3. 7H2O (1.0 g, 2.7 mmol) and NaBH4 (0.84 g, 22.5 mmol). The mixture was stirred for 0.5 h at −20° C., then poured into cold water (20 mL) and extracted with dichloromethane (2×15 mL). The solvent was removed by reduced pressure and the residue was purified by silica gel column (petroleum ether/ethyl acetate=5:1) to yield the title compound (0.55 g, 78%). H NMR (300 MHz, CDCl3): δ 7.64-7.60 (m, 2H), 7.25-7.22 (m, 2H), 5.67-5.61 (m, 1H), 5.07 (s, 1H), 4.98 (s, 1H), 3.21-3.09 (m, 2H), 2.81-2.56 (m, 5H); LC-MS: [M+1]+ 314.1.

후처리

  1. extractionextracted with dichloromethane (2×15 mL)
  2. customThe solvent was removed by reduced pressure
  3. customthe residue was purified by silica gel column (petroleum ether/ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-5cbf9c744613444f848ddbc9142de239
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501768B2

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