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

HRID 1640264노트

반응식

HRID 1640264 반응식
[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.C([Al]CC(C)C)C(C)C>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

참가 물질

6

반응물 3

HCID 16682954DibahHCID 21225700DiisobutylaluminumhydrideHCID 57974061HCID 57974061, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 8028Tetrahydrofuran용매

실험 절차

7.0 mL (7.0 mmol) of a 1 molar diisobutyl-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 the mixture was stirred for 20 h at RT. Then the reaction mixture was refluxed for 8 h. A 1 M diisobutylaluminium hdyride solution in toluene was added twice more and the mixture was refluxed for 8 h and 24 h, respectively. 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).

후처리

  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
  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)

출처 및 근거

ORD 기록
ord-113a9ea1b16944ec8256c58241b51771
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110575B2

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