Piperidine → Methyl 1-methylcyclohexanecarboxylate

HRID 1716520Notes

Reaction equation

HRID 1716520 reaction equation
[C:1](=O)([O-])O.[Na+].Cl.[CH3:7][O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14](CN)[CH2:13][CH2:12]1)=[O:10].C1C2C(COC(N=C=S)=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)(Cl)Cl>[CH3:7][O:8][C:9]([C:11]1([CH3:1])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:10]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 4154759Fmoc isothiocyanateHCID 178501119HCID 178501119, compound

Product 1

HCID 524785Methyl 1-methylcyclohexanecarboxylateYield 99.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Sodium hydrogen carbonate (1.68 g, 20.0 mmol) was added to a solution of trans-4-aminomethyl cyclohexanecarboxylic acid methyl ester hydrochloride (2.07 g, 10.0 mmol) obtained in Step 1, 9-fluorenylmethoxycarbonyl isothiocyanate (2.81 g, 10.0 mmol) in chloroform (40 ml) while ice-cooled. The reaction solution was stirred at room temperature for 16 hours, piperidine (5 ml, 50 mmol) was added, and the mixture was stirred at room temperature for further 6 hours. Trans-4-thiouredide methylcyclohexane carboxylic acid methyl ester (1.55 g, 67%) was obtained by concentrating the reaction solution in vacuo and purifying the obtained solid by silica gel column chromatography (ethyl acetate).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at room temperature for further 6 hours

Sources & evidence

ORD record
ord-362a7171533a46bf8992f765d291dada
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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