Sodium Hydroxide → HCID 59234220, compound

HRID 1942519Notes

Reaction equation

HRID 1942519 reaction equation
[C:1]1([C@H:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C@@H:8]2[C:20]([O:22]C)=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1.CO>[C:16]([O:15][C:13]([N:10]1[CH2:11][CH2:12][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C@@H:8]([C:20]([OH:22])=[O:21])[CH2:9]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86656364HCID 86656364, compound

Product 1

HCID 59234220HCID 59234220, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-tert-Butyl 3-methyl (3R,4S)-4-phenylpiperidine-1,3-dicarboxylate (585 mg) was dissolved in tetrahydrofuran (5 ml) and methanol (5 ml), and thereto was added 1M aqueous sodium hydroxide solution (5.5 ml), and the mixture was stirred at room temperature for 5 hours. The reaction solution was concentrated under reduced pressure, and thereto was added a 5% potassium hydrogen sulfate, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (546 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionwas added a 5% potassium hydrogen sulfate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb69f82f08ba427fabc3cb5b05d9a70a
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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