Hydrochloric Acid → (S)-1-(2-fluoro-4-(prop-1-en-2-yl)phenyl)ethanamine

HRID 57433ノート

反応式

HRID 57433 の反応式
[F:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:5]=[CH:4][C:3]=1[C@@H:11]([NH:13][S@@](C(C)(C)C)=O)[CH3:12].[ClH:20]>O1CCOCC1>[ClH:20].[F:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:5]=[CH:4][C:3]=1[C@@H:11]([NH2:13])[CH3:12]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 86730187(R)-N-((S)-1-(2-fluoro-4-(prop-1-en-2-yl)phenyl)ethyl)-2-methylpropane-2-sulfinamide

生成物 2

HCID 313Hydrochloric AcidHCID 90415150(S)-1-(2-fluoro-4-(prop-1-en-2-yl)phenyl)ethanamine収率 96%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

To a round bottom flask containing (R)—N—((S)-1-(2-fluoro-4-(prop-1-en-2-yl)phenyl)ethyl)-2-methylpropane-2-sulfinamide (1.02 g, 3.60 mmol) was added dioxane (7 mL). To this homogenous solution was then added HCl in Dioxane (1.80 mL, 7.20 mmol, 4 M). Resulting reaction mixture allowed to stir 10 min at room temperature. Volatiles removed. Et2O was added and mixture sonnicated briefly. Volatiles removed again. Et2O was added and the solid collected and washed with Et2O to afford a white HCl salt of (S)-1-(2-fluoro-4-(prop-1-en-2-yl)phenyl)ethanamine (742 mg, 3.44 mmol, 96% yield). 1H NMR (400 MHz, D2O) δ 1.65 (d, J=6.94 Hz, 3H) 2.12 (s, 3H) 5.23 (s, 1H) 5.50 (s, 1H) 7.37 (d, J=13.06 Hz, 1H) 7.43 (m, 2H). LCMS m/z 163.2 (deamino fragment) (M+H)+, Rt 0.56 min.

後処理

  1. customResulting
  2. customreaction mixture
  3. customVolatiles removed
  4. additionEt2O was added
  5. customVolatiles removed again
  6. additionEt2O was added
  7. customthe solid collected
  8. washwashed with Et2O

出典と根拠

ORDレコード
ord-2e3de750ceaa468fa0382b6ea5d225be
出典データセット
uspto-grants-2016_09
特許番号
US09434719B2

反応ノート

読み込み中…