Sodium sulfate decahydrate → 1-Methyl-3-(2-(4-(3-methoxyphenyl)butyl)phenoxymethyl)piperidine

HRID 743329ノート

反応式

HRID 743329 の反応式
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=2)[CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:33][O:32][C:28]1[CH:27]=[C:26]([CH2:25][CH2:24][CH2:23][CH2:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][CH:10]2[CH2:11][CH2:12][CH2:13][N:8]([CH3:6])[CH2:9]2)[CH:31]=[CH:30][CH:29]=1

参加物

5

反応物 3

HCID 62649Sodium sulfate decahydrateHCID 106473391-t-Butoxycarbonyl-3-{2-[4-(3-methoxyphenyl)butyl]phenoxymethyl}piperidineHCID 21226445Aluminium lithium hydride2 回

生成物 1

HCID 100012501-Methyl-3-(2-(4-(3-methoxyphenyl)butyl)phenoxymethyl)piperidine収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 2.70 g of 1-t-butoxycarbonyl-3-{2-[4-(3-methoxyphenyl)butyl]phenoxymethyl}piperidine [prepared as described in Example 82(a)] in 25 ml of tetrahydrofuran was added dropwise to a mixture of 0.450 g of lithium aluminum hydride in 30 ml of tetrahydrofuran, whilst ice-cooling and stirring, and the mixture was stirred at room temperature for 30 minutes and then stirred whilst heating under reflux for 2 hours. At the end of this time, the reaction mixture was cooled, and sodium sulfate decahydrate was added to the mixture to decompose excess lithium aluminium hydride. Insoluble materials were removed by filtration, and the filtrate was concentrated by distillation under reduced pressure. The resulting oil was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 2.10 g (yield 96%) of the title compound as a colorless oil.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. stirringstirred
  4. temperaturewhilst heating
  5. temperatureunder reflux for 2 hours
  6. temperatureAt the end of this time, the reaction mixture was cooled
  7. customInsoluble materials were removed by filtration
  8. concentrationthe filtrate was concentrated by distillation under reduced pressure
  9. customThe resulting oil was purified by column chromatography through silica gel
  10. additionby volume mixture of methylene chloride and methanol as the eluent

出典と根拠

ORDレコード
ord-098ea59c9bd44c91a655fbcf3cda29be
出典データセット
uspto-grants-1996_09
特許番号
US05556864

反応ノート

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