Water → 1-Benzyl-4-(pyridin-3-YL)piperidin-4-OL

HRID 1005207

反応式

HRID 1005207 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[CH2:13]([N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>COC(C)(C)C>[CH2:13]([N:20]1[CH2:25][CH2:24][C:23]([OH:26])([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

6

反応物 4

HCID 962WaterHCID 122863-BromopyridineHCID 192201-Benzyl-4-piperidoneHCID 178418339Butyllithium

生成物 1

HCID 10940791-Benzyl-4-(pyridin-3-YL)piperidin-4-OL収率 60%

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒2 回

反応条件

温度
-75 °C

実験手順

(α) A solution of 16.7 g (106 mmol) of 3-bromo-pyridine in 200 ml of tert-butyl methyl ether was cooled to -75° C. Thereto there was added dropwise within 45 minutes a solution of 66 ml (106 mmol) of n-butyllithium (1.6M in hexane) and the mixture was stirred at -75° C. for one hour. Subsequently, a solution of 10.0 g (52.8 mmol) of 1-benzyl-4-piperidone in 50 ml of tert-butyl methyl ether was added dropwise at -70° C. to -75° C. and thereafter the mixture was stirred for 2 hours. Subsequently, the mixture was left to warm to room temperature. Thereafter, it was hydrolyzed with 50 ml of water and extracted with 100 ml of ethyl acetate. The organic phase was dried over magnesium sulphate and finally the solvent was evaporated under reduced pressure, with the product beginning to separate. From the evaporated mother liquor there were isolated by crystallization from a mixture of ethyl acetate and hexane a further 1.9 g, so that a total of 8.4 g (60% of theory) of 1'-benzyl-2',3',5',6'-tetrahydro-1'H-[3,4']bipyridinyl-4'-ol were obtained as a colourless solid; MS: 268 (M+H)+.

後処理

  1. stirringthe mixture was stirred for 2 hours
  2. waitSubsequently, the mixture was left
  3. temperatureto warm to room temperature
  4. extractionextracted with 100 ml of ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. customfinally the solvent was evaporated under reduced pressure, with the product
  7. customto separate
  8. customFrom the evaporated mother liquor there were isolated by crystallization from a mixture of ethyl acetate and hexane a further 1.9 g

出典と根拠

ORDレコード
ord-3e831f5dfbfa4c19868461769383e172
出典データセット
uspto-grants-2000_04
特許番号
US06051712

関連ノート

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