Methanol → [(R)-6-fluoro-8-(2-methoxyphenyl)-3,4-dihydro-2H-chromen-2-yl]methanamine

HRID 902318

Reaktionsgleichung

Reaktionsgleichung von HRID 902318
[N:1]([CH2:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH:9]=[C:10]([F:15])[CH:11]=2)[O:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>O1CCCC1.O.C(C(Cl)Cl)C.[NH4+].[OH-]>[F:15][C:10]1[CH:11]=[C:12]2[C:7](=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH:9]=1)[O:6][C@@H:5]([CH2:4][NH2:1])[CH2:14][CH2:13]2

Komponenten

8

Edukt 3

HCID 887MethanolHCID 11776TriphenylphosphineHCID 86609113(R)-2-azidomethyl-8-(2-methoxyphenyl)-6-fluoro-chroman

Produkt 1

HCID 15942471[(R)-6-fluoro-8-(2-methoxyphenyl)-3,4-dihydro-2H-chromen-2-yl]methanamine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 65731,1-DichloropropaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 14923Ammonium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-(azidomethyl)-6-fluoro-8-(2-methoxyphenyl)-chroman (210 mg, 0.67 mmol) in tetrahydrofuran (15 mL) and water (0.5 mL) was added triphenylphosphine (0.21 g, 0.80 mmol) and the reaction mixture stirred at room temperature for 24 hours. Chromatography with 0–10% methanol in ethyl methylene chloride plus 1% NH4OH afforded [(R)-6-fluoro-8-(2-methoxyphenyl)-3,4-dihydro-2H-chromen-2-yl]methanamine as a colorless oil. The oil was dissolved in ethyl acetate and made into its hydrochloride salt (0.95 g, 69%) as a white solid using excess ethereal hydrochloric acid, mp 100° C. decomposed; MS (ES) m/z 288.1 ([M+H]+); [α]D25=−34.64° (c=5.7 mg/0.7 mL MeOH).

Quellen und Nachweise

ORD-Eintrag
ord-8e5b20030d6648e7a7c80d65b2bf6a29
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365095B2

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