Triphenylphosphine → WAY-261240

HRID 902306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902306
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[O:17][C@@H:16]([CH2:19][N:20]=[N+]=[N-])[CH2:15][CH2:14]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[O:17][C@@H:16]([CH2:19][NH2:20])[CH2:15][CH2:14]2

Komponenten

5

Edukt 2

HCID 11776TriphenylphosphineHCID 86609105HCID 86609105, Verbindung

Produkt 1

HCID 17747578WAY-261240Ausbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of {[(2R)-8-(2,6-dichlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl}azide (0.21 g, 0.628 mmol) in tetrahydrofuran (10 mL) and water (1 mL) was added polymer-bound triphenylphosphine (˜3 mmol/g, 0.628 g, 1.885 mmol) and the reaction mixture stirred at room temperature for 4 days. The brown suspension was then filtered through celite, the filter cake washed with ethyl acetate (50 mL) and the combined filtrates concentrated under reduced pressure to afford a yellow syrup. Purification by flash chromatography using a solvent gradient of 0.5 to 5% ammonia saturated methanol solution in dichloromethane gave 159 mg (82%) of {[(2R)-8-(2,6-dichlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl}amine as a colorless syrup. The product was dissolved in 2-propanol (1 mL) and diethyl ether (2.5 mL) and a solution of hydrogen chloride (1.0 M in diethyl ether, 0.517 mL, 0.517 mmol) was added followed by hexane (2 mL). The resulting white precipitate was filtered to afford 155 mg (72%) of {[(2R)-8-(2,6-dichlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl}amine hydrochloride as a white crystalline solid, mp 188–190° C.; [α]D25=−6.74° (c=5.4 mg/0.7 mL MeOH).

Aufarbeitung

  1. filtrationThe brown suspension was then filtered through celite
  2. washthe filter cake washed with ethyl acetate (50 mL)
  3. concentrationthe combined filtrates concentrated under reduced pressure
  4. customto afford a yellow syrup
  5. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-459e25dfd54043dda6494f39f1801339
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365095B2

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