Methanol → {[(R)-8-(2-methoxyphenyl)-6-fluoro-2H-chromen-2-yl]methyl}amine

HRID 902337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902337
[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(Cl)Cl.[NH4+].[OH-]>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:8]1[CH:9]=[C:10]([F:15])[CH:11]=[C:12]2[C:7]=1[O:6][C@@H:5]([CH2:4][NH2:1])[CH:14]=[CH:13]2

Komponenten

8

Edukt 3

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

Produkt 1

HCID 59701548{[(R)-8-(2-methoxyphenyl)-6-fluoro-2H-chromen-2-yl]methyl}amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 14923Ammonium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-azidomethyl-8-(2-methoxyphenyl)-6-fluoro-chroman (190 mg, 0.32 mmol) in tetrahydrofuran (10 mL) and water (0.5 mL) was added triphenylphosphine (0.26 g, 10 mmol) and the reaction mixture stirred at room temperature for 24 hours. The solvent was removed under vacuum to form a colorless oil. Chromatography with 0–5% methanol in methylene chloride plus 1% NH4OH afforded {[(R)-8-(2-methoxyphenyl)-6-fluoro-2H-chromen-2-yl]methyl}amine as a colorless oil. The colorless oil was dissolved in ethyl acetate and made into its hydrochloride salt (119 mg, 61%) as an off-white crystalline solid, mp 198–200° C.; [α]D25=+173.89° (c=5.2 mg/0.7mL MeOH).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customto form a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-df21f2ee12534b0d992aa75e82bebba5
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365095B2

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