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

HRID 57433노트

반응식

HRID 57433 반응식
[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]

참가 물질

5

반응물 2

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

생성물 2

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2e3de750ceaa468fa0382b6ea5d225be
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

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