Aluminium lithium hydride → (R)-4-[2-(1-Methyl-2,2,2-trifluoroethylamino)-thiazol-4-yl]-benzylamine

HRID 1191081노트

반응식

HRID 1191081 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C@@H:8]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[N:18]=1)[C:9]([F:12])([F:11])[F:10]>C1COCC1>[CH3:7][C@@H:8]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=2)[N:18]=1)[C:9]([F:10])([F:12])[F:11]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 86624159(R)-4-[2-(1-Methyl-2,2,2-trifluoroethylamino)-thiazol-4-yl]-benzonitrile

생성물 1

HCID 59828830(R)-4-[2-(1-Methyl-2,2,2-trifluoroethylamino)-thiazol-4-yl]-benzylamine수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Add a solution of 1M lithium aluminum hydride in THF (12 mL, 12 mmol) dropwise to an ice-cooled solution of (R)-4-[2-(1-methyl-2,2,2-trifluoroethylamino)-thiazol-4-yl]-benzonitrile in anhydrous THF (10 mL). Heat to reflux for 1 h, cool to room temperature, quench by slow addition of water (12 mL), ether (50 mL), 1N NaOH (12 mL) and additional water (36 mL). Add EtOAc (50 mL), stir vigorously for 20 min and filter over a bed of Celite®. Dry the organic phase over MgSO4, filter and concentrate in vacuo to obtain the title compound (765 mg, 64%). MS (ES+) m/z: 302 (M+H)+.

후처리

  1. temperatureHeat
  2. temperatureto reflux for 1 h
  3. customquench by slow addition of water (12 mL), ether (50 mL), 1N NaOH (12 mL) and additional water (36 mL)
  4. filtrationfilter over a bed of Celite®
  5. dry with materialDry the organic phase over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

출처 및 근거

ORD 기록
ord-518555e7399a4df282d3260dc20c0cd4
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680091B2

반응 노트

불러오는 중…