4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinebutanoic acid ethyl ester → HCID 15042243, compound

HRID 973415Notes

Reaction equation

HRID 973415 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[OH:15])[CH2:10][CH2:9]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:14]([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)([OH:15])[CH:11]2[CH2:12][CH2:13][N:8]([CH2:7][CH2:6][CH2:5][CH2:4][OH:3])[CH2:9][CH2:10]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 150422374-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinebutanoic acid ethyl esterHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 15042243HCID 15042243, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15.4 g (0.037 mol) of 4-[bis(4-fluorophenyl)hydroxymethyl]-1-piperidinebutanoic acid ethyl ester in 100 mL of dry (freshly distilled from lithium aluminum hydride) tetrahydrofuran was added dropwise to a mixture of 3.5 g (0.092 mol) of lithium aluminum hydride in 100 mL of dry tetrahydrofuran. After the final addition, the mixture was stirred at ambient temperature for 3 h, whereupon the excess lithium aluminum hydride was quenched by successive dropwise additions of 4 mL of water, 4 mL of 15% sodium hydroxide solution and 12 mL of water. The mixture was stirred for 30 min, filtered, and the filtrate concentrated under reduced pressure to yield 11.2 g (100%) of an oil which crystallized upon standing. A portion of the solid was recrystallized from ethyl acetate/petroleum ether (30°-60° C.) to give the title compound as a light-tan solid, mp 130°-131° C.

Workup

  1. distillationfreshly distilled from lithium aluminum hydride) tetrahydrofuran
  2. additionAfter the final addition
  3. customwas quenched by successive dropwise additions of 4 mL of water, 4 mL of 15% sodium hydroxide solution and 12 mL of water
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-932630fc6d6e4c2692892dcd48288212
Source dataset
uspto-grants-1991_11
Patent number
US05063235

Reaction notes

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