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

HRID 1365517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1365517
[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

Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ac1895b858e04f39b884c007607419d8
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888376B2

Notizen zur Reaktion

Wird geladen…