Diisobutylaluminumhydride → (S)-2-(3,5-difluorophenyl)-5,5-dimethylpiperidine

HRID 74616ノート

反応式

HRID 74616 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[F:11][C:12]1[CH:13]=[C:14]([C@H:19]2[NH:24][C:23](=O)[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20]2)[CH:15]=[C:16]([F:18])[CH:17]=1>C1(C)C=CC=CC=1.C1COCC1>[F:18][C:16]1[CH:15]=[C:14]([C@@H:19]2[CH2:20][CH2:21][C:22]([CH3:27])([CH3:26])[CH2:23][NH:24]2)[CH:13]=[C:12]([F:11])[CH:17]=1

参加物

5

反応物 2

HCID 21225700Diisobutylaluminumhydride2 回HCID 57974061HCID 57974061、化合物

生成物 1

HCID 66722231(S)-2-(3,5-difluorophenyl)-5,5-dimethylpiperidine

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

7.0 mL (7.0 mmol) of a 1 molar di-isobutyl-aluminium hydride solution in toluene were added to 0.48 g (2.0 mmol) (S)-6-(3,5-difluorophenyl)-3,3-dimethylpiperidin-2-one in 10 mL THF while cooling with ice and stirred for 20 h at RT. Then the reaction mixture was refluxed for 8 h. A 1M diisobutylaluminium hydride solution in toluene was added twice more and the mixture was refluxed for 8 h and 24 h in each case. After hydrolysis of the reaction mixture the precipitate formed was suction filtered and washed with THF. The filtrate was evaporated down and the residue was purified by flash chromatography (aluminium oxide).

後処理

  1. temperaturewhile cooling with ice
  2. temperatureThen the reaction mixture was refluxed for 8 h
  3. temperaturethe mixture was refluxed for 8 h and 24 h in each case
  4. customAfter hydrolysis of the reaction mixture the precipitate
  5. customformed
  6. filtrationfiltered
  7. washwashed with THF
  8. customThe filtrate was evaporated down
  9. customthe residue was purified by flash chromatography (aluminium oxide)

出典と根拠

ORDレコード
ord-0fc481b970a945f3b82122cf544fecbd
出典データセット
uspto-grants-2014_09
特許番号
US08829006B2

反応ノート

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