Hydrazine hydrate (1:1) → (S)-2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanamine

HRID 2279452노트

반응식

HRID 2279452 반응식
[Si:1]([O:8][CH2:9][C@@H:10]([N:19]1C(=O)C2C(=CC=CC=2)C1=O)[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([F:18])[CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1COCC1.CO.O.NN>C1COCC1>[Si:1]([O:8][CH2:9][C@H:10]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([F:18])[CH:12]=1)[NH2:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 24654Hydrazine hydrate (1:1)HCID 21899815MeOH tetrahydrofuranHCID 68294575(S)-2-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)isoindoline-1,3-dione

생성물 1

HCID 86705474(S)-2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanamine수율 88.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of 66 (14.35 g, 33.07 mmol) and THF/MeOH (1:1, 400 mL) was added hydrazine monohydrate (4.138 g, 82.67 mmol) and the reaction was heated to 60° C. for 3 h. The reaction was diluted with THF and filtered. The solid was discarded and the filtrate was concentrated and the residue dissolved in ether (200 mL). The organic layer was washed twice with water (100 mL). The organic layer was then dried, filtered and concentrated. The crude product was purified by SiO2 (Biotage 65) eluting with an EtOAc/hexane gradient (30 to 40% EtOAc) to afford 8.85 g (88.1%) of (S)-2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanamine (68).

후처리

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. dissolutionthe residue dissolved in ether (200 mL)
  4. washThe organic layer was washed twice with water (100 mL)
  5. customThe organic layer was then dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by SiO2 (Biotage 65)
  9. washeluting with an EtOAc/hexane gradient (30 to 40% EtOAc)

출처 및 근거

ORD 기록
ord-95207e8033b44c8b936dceda5caea946
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

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