Water → HCID 21993816, compound

HRID 1978336Notes

Reaction equation

HRID 1978336 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH:13]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:24][CH2:23][CH:22]([C:25](OC)=[O:26])[CH2:21][CH2:20]3)[CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C.O>O1CCCC1>[C:7]1([CH:13]2[CH2:14][CH2:15][N:16]([CH:19]3[CH2:24][CH2:23][CH:22]([CH2:25][OH:26])[CH2:21][CH2:20]3)[CH2:17][CH2:18]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2×HCID 21993968HCID 21993968, compound

Product 1

HCID 21993816HCID 21993816, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.36 g (9.37 mM) of lithium aluminum hydride in 50 ml of tetrahydrofuran was added a solution of 2.825 g (9.372 mM) of methyl 4-(4-phenylpiperidino)cyclohexanecarboxylate in 50 ml of tetrahydrofuran dropwise with ice-cooling and the mixture was stirred at room temperature for one hour. To this reaction mixture was added ethyl acetate with ice-cooling to decompose the excess lithium aluminum hydride. Then, water was added until a white precipitate had formed. The precipitate was filtered off with the aid of celite and washed with ethyl acetate. The filtrate and washes were pooled and the solvent was distilled off under reduced pressure. The solid residue was rinsed with diethyl ether-hexane to provide the title compound.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customhad formed
  4. filtrationThe precipitate was filtered off with the aid of celite
  5. washwashed with ethyl acetate
  6. distillationthe solvent was distilled off under reduced pressure
  7. washThe solid residue was rinsed with diethyl ether-hexane

Sources & evidence

ORD record
ord-db94d560ff9c471a94c1c2901cb3167b
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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