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

HRID 1937430Notes

Reaction equation

HRID 1937430 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-46ede23a01b04d258f5075419fa1d60b
Source dataset
uspto-grants-2002_05
Patent number
US06395748B2

Reaction notes

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