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

HRID 2279452ノート

反応式

HRID 2279452 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-95207e8033b44c8b936dceda5caea946
出典データセット
uspto-grants-2015_09
特許番号
US09133187B2

反応ノート

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