Hydrochloric Acid → (R)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethanamine

HRID 1365517Notes

Reaction equation

HRID 1365517 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@:15]([NH:30][S@@](C(C)(C)C)=O)([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[C:6]([O:8][C:9]([F:14])([F:13])[CH:10]([F:12])[F:11])[CH:7]=1.Cl>CO.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C@@:15]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)([NH2:30])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[C:6]([O:8][C:9]([F:14])([F:13])[CH:10]([F:12])[F:11])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59458565(R)-N-((R)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 59458485(R)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethanamineYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)—N—((R)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)-2-methylpropane-2-sulfinamide (38 mg, 0.081 mmol) in methanol (0.2 mL) was added 4N HCl in dioxane (0.2 mL). The resulting reaction was stirred at room temperature for 5 minutes and the solvent was evaporated under reduced pressure. The crude product was diluted in EtOAc and washed with sat'd. NaHCO3 and dried over Na2SO4. The EtOAc was evaporated under reduced pressure and pumped to dryness to afford (R)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethanamine (26 mg, 92% yield) as a colorless oil. LC-MS (ESI) 345.17 (M+H−17), 362.19 (M+H), retention time=3.26 minutes (0-100% MeOH/H2O/0.1% TFA, 4 min run).

Workup

  1. customThe resulting reaction
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe crude product was diluted in EtOAc
  4. washwashed with sat'd
  5. dry with materialNaHCO3 and dried over Na2SO4
  6. customThe EtOAc was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ac1895b858e04f39b884c007607419d8
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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