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

HRID 57433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57433
[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]

Komponenten

5

Edukt 2

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

Produkt 2

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2e3de750ceaa468fa0382b6ea5d225be
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434719B2

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