Sodium Hydroxide → HCID 57686979, compound

HRID 547499Notes

Reaction equation

HRID 547499 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH:13]3[CH2:20][C:19]4([C:21]([O:23]CC)=[O:22])[CH:15]([CH2:16][CH2:17][CH2:18]4)[CH2:14]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.O>[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([CH:13]3[CH2:20][C:19]4([C:21]([OH:23])=[O:22])[CH:15]([CH2:16][CH2:17][CH2:18]4)[CH2:14]3)[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57686976HCID 57686976, compound

Product 1

HCID 57686979HCID 57686979, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-phenylpiperidin-1-yl)octahydropentalene-3a-carboxylate (1.85 g, 5.42 mmol) in THF (35 mL) was added a solution of sodium hydroxide (2.16 g, 54.2 mmol) in water (35 mL). The reaction mixture was stirred at ambient temperature for about 18 h. The solvent was removed under reduced pressure and the crude product was extracted into DCM (3×20 mL). The combined organic phases were washed with water (3×50 mL) and dried over MgSO4. Concentration in vacuo gave 2-(4-phenyl-piperidin-1-yl)-hexahydro-pentalene-3a-carboxylic acid (1.70 g) that was used in the next step without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe crude product was extracted into DCM (3×20 mL)
  3. washThe combined organic phases were washed with water (3×50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-1f5b9143a3bb421fa3e3dce313af1f5a
Source dataset
uspto-grants-2011_05
Patent number
US07939544B2

Reaction notes

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