Water → HCID 58692401, compound

HRID 2054457Notes

Reaction equation

HRID 2054457 reaction equation
[OH2:1].[OH-:2].[K+].[C:4]([CH2:6][C:7]1([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([CH3:27])[CH:21]=2)[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)#N>C(O)C>[C:16]([O:15][C:13]([N:10]1[CH2:11][CH2:12][C:7]([CH2:6][C:4]([OH:2])=[O:1])([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([CH3:27])[CH:21]=2)[CH2:8][CH2:9]1)=[O:14])([CH3:18])([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 58692361HCID 58692361, compound

Product 1

HCID 58692401HCID 58692401, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Water (50 mL) and potassium hydroxide (11.9 g, 213 mmol) were added to a solution of tert-butyl 4-(cyanomethyl)-4-(3,4-dimethylphenyl)piperidine-1-carboxylate 8-4 (14.0 g, 42.6 mmol) in ethanol (200 mL). The reaction was heated at approximately 90° C. until complete conversion of starting material (as monitored by high-pressure liquid chromatography). The reaction mixture was then cooled to ambient temperature, quenched with ice cold 1 N aqueous hydrochloric acid (500 mL) and extracted with ethyl acetate (3×500 mL). The organic phase was washed with brine, dried (magnesium sulfate) and concentrated in vacuo to give a crude residue. Purification of the crude residue by flash chromatography over silica gel (gradient elution; 20%-40% ethyl acetate/hexanes as eluent) afforded compound 8-5 as a white solid.

Workup

  1. temperatureThe reaction mixture was then cooled to ambient temperature
  2. customquenched with ice cold 1 N aqueous hydrochloric acid (500 mL)
  3. extractionextracted with ethyl acetate (3×500 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customto give a crude residue
  8. customPurification of the crude residue by flash chromatography over silica gel (gradient elution; 20%-40% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-1d93c76867774955bac21ce4c3e436fd
Source dataset
uspto-grants-2008_02
Patent number
US07329673B2

Reaction notes

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