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 1930224ノート

反応式

HRID 1930224 の反応式
[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]

参加物

5

反応物 3

HCID 24758Sodium hydride2 回HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 576525476-Fluoro-2-[(4-methoxyphenyl)methyl]-7-phenylisoquinolin-1(2H)-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-42d6b429e4c94eb48daf99b78af0fd48
出典データセット
uspto-grants-2012_05
特許番号
US08188117B2

反応ノート

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