4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinepentanoic acid ethyl ester → HCID 67928225, compound

HRID 973416Notes

Reaction equation

HRID 973416 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[OH:16])[CH2:11][CH2:10]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH2:3].[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:15]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)([OH:16])[CH:12]2[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][OH:3])[CH2:10][CH2:11]2)=[CH:22][CH:21]=1.[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]([CH:12]2[CH2:13][CH2:14][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][OH:3])[CH2:10][CH2:11]2)([OH:16])[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 150422384-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinepentanoic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 67928225HCID 67928225, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 16.8 g (0.040 mol) of 4-[bis(4-fluorophenyl)hydroxymethyl]-1-piperidinepentanoic acid ethyl ester in 100 mL of dry (freshly distilled from lithium aluminum hydride) tetrahydrofuran was added dropwise to a solution of 3.8 g (0.100 mol) of lithium aluminum hydride in 100 mL of dry tetrahydrofuran while stirring vigorously at ambient temperature for 1 h and the excess lithium aluminum hydride was quenched by successive, dropwise additions of 4 mL of water, 4 mL of a 15% sodium hydroxide solution, and 12 mL of water. The solution was allowed to stir for 30 min, filtered, and the filtrate concentrated under reduced pressure to yield 11.5 g (98%) of an off-white solid. A portion of the solid was recrystallized from ethyl acetate/petroleum ether (30°-60° C.) to give the title compound as a white solid, mp 103°-105° C.

Workup

  1. distillationfreshly distilled from lithium aluminum hydride) tetrahydrofuran
  2. customthe excess lithium aluminum hydride was quenched by successive, dropwise additions of 4 mL of water, 4 mL of a 15% sodium hydroxide solution, and 12 mL of water
  3. stirringto stir for 30 min
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-bd5bd4e7a3e64d139345bf713e51a0c3
Source dataset
uspto-grants-1991_11
Patent number
US05063235

Reaction notes

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