Sodium hydride → 4-[2-(4-Methoxy-benzyl)-1-oxo-7-phenyl-1,2-dihydro-isoquinolin-6-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1930224노트

반응식

HRID 1930224 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].F[C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:24](=[O:34])[N:23]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)[CH:22]=[CH:21]2>CC(N(C)C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][C:27]=2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:24](=[O:34])[N:23]([CH2:35][C:36]2[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=2)[CH:22]=[CH:21]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 24758Sodium hydride2회HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 576525476-Fluoro-2-[(4-methoxyphenyl)methyl]-7-phenylisoquinolin-1(2H)-one

생성물 1

HCID 576525764-[2-(4-Methoxy-benzyl)-1-oxo-7-phenyl-1,2-dihydro-isoquinolin-6-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

실험 절차

168 mg (0.83 mmol) 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester were dissolved in 5 mL of dimethylacetamide and 20 mg (0.83 mmol) of sodium hydride (60%) were added. The mixture was stirred at room temperature. After 30 minutes a solution of 240 mg (0.67 mmol) 6-fluoro-2-(4-methoxy-benzyl)-7-phenyl-2H-iso-quinolin-1-one (315) in 5 mL of dimethylacetamide was added and stirring was continued at room temperature. After standing overnight, 20 mg (0.83 mmol) of sodium hydride (60%) were added and the solution was stirred at 100° C. After 1 h, the solvent was removed i. vac. and saturated sodium bicarbonate solution was added. The aqueous phase was extracted three times with dichloromethane. The organic layers were dried with MgSO4 and evaporated. The crude product was purified by preparative HPLC. Rt=1.98 min (Method C). Detected mass: 541.7 (M+H+).

후처리

  1. stirringstirring
  2. customwas continued at room temperature
  3. stirringthe solution was stirred at 100° C
  4. waitAfter 1 h
  5. customthe solvent was removed i
  6. additionand saturated sodium bicarbonate solution was added
  7. extractionThe aqueous phase was extracted three times with dichloromethane
  8. dry with materialThe organic layers were dried with MgSO4
  9. customevaporated
  10. customThe crude product was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-42d6b429e4c94eb48daf99b78af0fd48
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188117B2

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