Hydrochloric Acid → (S)-1-(4-(1-aminoethyl)-3-fluorophenyl)ethanone

HRID 57438Notes

Reaction equation

HRID 57438 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]([NH:14][S@@](C(C)(C)C)=O)[CH3:13])=[C:8]([F:21])[CH:7]=1)=[CH2:5])C.Cl>CO>[NH2:14][C@H:12]([C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:3])[CH3:5])=[CH:7][C:8]=1[F:21])[CH3:13]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86730184(R)-N-((S)-1-(4-(1-ethoxyvinyl)-2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 90414323(S)-1-(4-(1-aminoethyl)-3-fluorophenyl)ethanoneYield 103.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round bottom flask containing (R)—N—((S)-1-(4-(1-ethoxyvinyl)-2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (600 mg, 1.91 mmol) was added MeOH (19 mL). To this homogenous solution was then added HCl (aq) (3.2 mL, 19.1 mmol, 3 M). Resulting reaction mixture was stirred at room temperature for 30 min. Volatiles were then removed. Residue triturated with Et2O to provide (S)-1-(4-(1-aminoethyl)-3-fluorophenyl)ethanone (0.43 g, 1.98 mmol, 103% yield) as a HCl salt. 1H NMR (400 MHz, D2O) δ 1.67 (d, J=6.99 Hz, 3H) 2.64 (s, 3H) 4.80-4.87 (m, 1H) 7.61 (t, J=7.73 Hz, 1H) 7.77 (dd, J=11.30, 1.66 Hz, 1H) 7.87 (dd, J=8.09, 1.64 Hz, 1H). LCMS m/z 182.0 (M+H)+, Rt 0.36 min.

Workup

  1. customResulting
  2. customreaction mixture
  3. customVolatiles were then removed
  4. customResidue triturated with Et2O

Sources & evidence

ORD record
ord-17496f7181a64d59933aefa0432bbabd
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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