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

HRID 1598014

Reaktionsgleichung

Reaktionsgleichung von HRID 1598014
[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 completed 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 oil. The title compound precipitated upon trituration with pentane as white crystals, m.p. 79°-80° 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 oil
  5. customThe title compound precipitated upon trituration with pentane as white crystals, m.p. 79°-80° C.

Quellen und Nachweise

ORD-Eintrag
ord-e53563257fdc40f58168d09f8e494947
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05736556

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