Ethyl 3-oxo-1-(phenylmethyl)-4-piperidinecarboxylate → HCID 13903343, compound

HRID 1246712Notes

Reaction equation

HRID 1246712 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]>C(OCC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]([OH:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 419705Ethyl 3-oxo-1-(phenylmethyl)-4-piperidinecarboxylateHCID 3028194Lithium

Product 1

HCID 13903343HCID 13903343, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

Ethyl 1-benzyl-3-oxo-4-piperidinecarboxylate (1.0 g, 3.8 mmol) in diethyl ether (50 mL) was treated with lithium aluminumhydride (150 mg, 3.9 mmol) at and −78° C. After stirring at −78° C. for 30 minutes, the mixture was allowed to warm to room temperature over 2 hours. The mixture was quenched with saturated ammonium chloride. Standard work-up gave a crude product which was purified via chromatography (SiO2, ethyl acetate:hexanes, 1:6) to provide the title compound. MS (EI, M+H)+264.

Workup

  1. temperatureto warm to room temperature over 2 hours
  2. customThe mixture was quenched with saturated ammonium chloride
  3. customStandard work-up gave a crude product which
  4. customwas purified via chromatography (SiO2, ethyl acetate:hexanes, 1:6)

Sources & evidence

ORD record
ord-b7e6376e1f7a4300b0c8a5cd155b867e
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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