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

HRID 1712695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712695
[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.CO>Cl.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 887MethanolHCID 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 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(R)—N—((R)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)-2-methylpropane-2-sulfinamide (234 mg, 0.442 mmol) was stirred in 4N HCl in dioxane (1.5 mL) and MeOH (1.5 mL) at room temperature under Ar for 10 min. The reaction mixture was concentrated, and then purified by flash chromatography (silica gel, hexanes/EtOAc) to give (R)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethanamine (169 mg, 90%). LC-MS (ESI) 409.16 (M−NH3+H), retention time=3.26 minutes (0-100% MeOH in H2O with 0.1% TFA in 4-min run); Analytical HPLC: 2.52 minutes (0-100% CH3CN in H2O with 0.1% TFA in 4-min run); 1H NMR (400 MHz, CD3OD) δ ppm 7.29-7.50 (m, 2H), 6.87-7.22 (m, 8H), 6.77 (d, J=6.15 Hz, 2H), 6.04-6.48 (m, 1H), 3.57 (s, 2H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatography (silica gel, hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-7892769f8e5140b98b6dff94ce74342d
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790770B2

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