Win 35428 → (1R,2S,3S)-2-Hydroxymethyl-3-(4-fluorophenyl)tropane

HRID 1492423

Reaktionsgleichung

Reaktionsgleichung von HRID 1492423
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C@H:11]1[C@@H:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:16][C@H:15]2[N:25]([CH3:26])[C@@H:12]1[CH2:13][CH2:14]2)(OC)=[O:8]>C(OCC)C>[OH:8][CH2:7][C@H:11]1[C@@H:17]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH2:16][C@H:15]2[N:25]([CH3:26])[C@@H:12]1[CH2:13][CH2:14]2

Komponenten

4

Edukt 2

HCID 105056Win 35428HCID 21226445Aluminium lithium hydride

Produkt 1

HCID 10514771(1R,2S,3S)-2-Hydroxymethyl-3-(4-fluorophenyl)tropane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a suspension of lithium aluminum hydride (0.8 g, 21 mmol) in diethyl ether (30 ml), at room temperature, was slowly added a solution of (1R,2S,3S)-2-carbomethoxy-3-(4-fluorophenyl)tropane (5 g, 18 mmol) in 100 ml diethyl ether. The reaction completes after stirring for 10 minutes and was quenched by addition of 0.8 ml water, 0.8 ml sodium hydroxide (15%) and 2 ml water. The aluminum salts were removed by filtration and the solvent was removed in vacuo leaving an oil. The title compound precipitates upon trituration with pentane as white crystals, m.p. 79°-180° C.

Aufarbeitung

  1. customwas quenched by addition of 0.8 ml water, 0.8 ml sodium hydroxide (15%) and 2 ml water
  2. customThe aluminum salts were removed by filtration
  3. customthe solvent was removed in vacuo
  4. customleaving an oil
  5. customThe title compound precipitates upon trituration with pentane as white crystals, m.p. 79°-180° C.

Quellen und Nachweise

ORD-Eintrag
ord-d7cba428f6044e218344d04fc1fd1581
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05374636

Verknüpfte Notizen

Wird geladen…