Water → 1-Acetyl-5-(cyclohexylmethyl)piperidine-3-carboxylic acid

HRID 1696286Notes

Reaction equation

HRID 1696286 reaction equation
[Li+].[OH-].[C:3]([N:6]1[CH2:11][CH:10]([CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:9][CH:8]([C:19]([O:21]CC)=[O:20])[CH2:7]1)(=[O:5])[CH3:4].C(Cl)Cl.O>CO.C1COCC1>[C:3]([N:6]1[CH2:11][CH:10]([CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:9][CH:8]([C:19]([OH:21])=[O:20])[CH2:7]1)(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 66844834Ethyl 1-acetyl-5-(cyclohexylmethyl)piperidine-3-carboxylate

Product 1

HCID 668447521-Acetyl-5-(cyclohexylmethyl)piperidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (2 N, 500 μL) was added to a solution of ethyl 1-acetyl-5-(cyclohexylmethyl)piperidine-3-carboxylate (180 mL, 0.61 mmol) in MeOH (1 mL) and THF (5 mL). After being maintained for two hours, the reaction was poured into a mixture of CH2Cl2 (25 mL) and H2O (10 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (10 mL). The aqueous layer was acidified to pH 1 with 1N HCl and extracted with CH2Cl2 (3×20 mL). The combined organic layers were sequentially washed with H2O (10 mL) and brine before being dried over Na2SO4. Concentration under reduced pressure provided the title compound as a colorless oil. MS m/z: 268.0 (M+1).

Workup

  1. temperatureAfter being maintained for two hours
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (10 mL)
  4. extractionextracted with CH2Cl2 (3×20 mL)
  5. washThe combined organic layers were sequentially washed with H2O (10 mL) and brine
  6. dry with materialbefore being dried over Na2SO4
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-f6168cb62aba4ba6aa29620ee20de220
Source dataset
uspto-grants-2012_04
Patent number
US08163766B2

Reaction notes

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