Potassium Hydroxide → 5-methyl-5-[(3S)-3-phenoxypyrrolidin-1-yl]-2,2-diphenylhexanamide

HRID 500616Notes

Reaction equation

HRID 500616 reaction equation
[OH-:1].[K+].[CH3:3][C:4]([N:23]1[CH2:27][CH2:26][C@H:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24]1)([CH3:22])[CH2:5][CH2:6][C:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:8]#[N:9]>CC(O)(CC)CC>[CH3:22][C:4]([N:23]1[CH2:27][CH2:26][C@H:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24]1)([CH3:3])[CH2:5][CH2:6][C:7]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:8]([NH2:9])=[O:1]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 547579545-Methyl-5-[(3S)-3-phenoxypyrrolidin-1-yl]-2,2-diphenylhexanenitrile

Product 1

HCID 160651355-methyl-5-[(3S)-3-phenoxypyrrolidin-1-yl]-2,2-diphenylhexanamideYield 82%

Reagents, catalysts & solvents 1

HCID 64933-Methyl-3-pentanolSolvent

Procedure

Potassium hydroxide (5.10 g, 91.98 mmol) was added to a solution of the product of example 1 (1.959, 4.60 mmol) in 3-methyl-3-pentanol (40 mL) and the mixture was heated under reflux for 24 hours. The reaction mixture was then cooled to room temperature, concentrated in vacuo and the residue was partitioned between ethyl acetate (70 mL) and water (40 mL). The aqueous layer was separated, extracted with ethyl acetate (50 mL) and the combined organic solution was dried over sodium sulfate and concentrated in vacuo. The residue was then re-crystallised from hexane/ethyl acetate and dried under vacuum for 18 hours to afford the title compound as a white solid in 82% yield, 1.66 g.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. concentrationconcentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate (70 mL) and water (40 mL)
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate (50 mL)
  7. dry with materialthe combined organic solution was dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was then re-crystallised from hexane/ethyl acetate
  10. customdried under vacuum for 18 hours

Sources & evidence

ORD record
ord-3918a8bd4f8e46cfb132c0bb489c073a
Source dataset
uspto-grants-2010_08
Patent number
US07772223B2

Reaction notes

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