1-Aminocyclohexanecarboxylic acid → Methyl 1-aminocyclohexanoate

HRID 1409543Notes

Reaction equation

HRID 1409543 reaction equation
[NH2:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:11][Si](C=[N+]=[N-])(C)C>O1CCCC1CO>[NH2:1][C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 13661-Aminocyclohexanecarboxylic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 4048819Methyl 1-aminocyclohexanoateYield 52%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

To a solution of 1-aminocyclohexanecarboxylic acid (600 mg) in tetrahydrofuran-methanol was added dropwise trimethylsilyl diazomethane (4.2 mL) under ice-cooling and stirring, and the mixture was stirred overnight. The reaction mixture was concentrated in vacuo, and to the residue were added successively diethylether-hexane (1/1) and a solution of 4N hydrochloric acid in ethyl acetate (1.05 mL). The precipitates were collected by filtration and dried to give methyl 1-amino-cyclohexanecarboxylate (423 mg, yield: 52%) as a white powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionto the residue were added successively diethylether-hexane (1/1)
  5. filtrationThe precipitates were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-dac9481abc714010ba21cf2f5cbac49c
Source dataset
uspto-grants-2014_12
Patent number
US08921380B2

Reaction notes

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