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

HRID 1598014

Reaction equation

HRID 1598014 reaction equation
[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

Participants

4

Reactant 2

HCID 105056Win 35428HCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-e53563257fdc40f58168d09f8e494947
Source dataset
uspto-grants-1998_04
Patent number
US05736556

Linked notes

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