Sodium Hydroxide → HCID 57686979, compound

HRID 1908212Notes

Reaction equation

HRID 1908212 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-b748b9ebdfa54cdd8dae101bdc18ff09
Source dataset
uspto-grants-2013_12
Patent number
US08598199B2

Reaction notes

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