1-Aminocyclohexanecarboxylic acid → HCID 86627846, compound

HRID 253062Notes

Reaction equation

HRID 253062 reaction equation
N[C:2]1([C:8]([OH:10])=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C[Si](C=[N+:16]=[N-])(C)C.O1CCCC1[CH2:23][OH:24]>>[NH2:16][C:3]1([O:24][CH3:23])[CH2:4][CH2:5][CH2:6][CH2:7][C:2]1=[C:8]=[O:10]

Participants

4

Reactant 3

HCID 13661-Aminocyclohexanecarboxylic acidHCID 7360Tetrahydrofurfuryl alcoholHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 86627846HCID 86627846, compoundYield 52%

Procedure

A solution of 1-aminocyclohexanecarboxylic acid (600 mg) in tetrahydrofuran-methanol was stirred under ice-cooling. Thereto was added dropwise a (trimethylsilyl) diazomethane solution (4.2 mL) and the mixture was stirred overnight. The reaction mixture was concentrated in vacuo and to the residue was added diethyl ether-hexane (1/1). Thereto was added 4M HCl-ethyl acetate (1.05 mL) and the precipitates were collected by filtration and dried to give 1-amino-1-methoxy-carbonylcyclohexane (423 mg, yield: 52%) as a white powder.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated in vacuo and to the residue
  3. additionwas added diethyl ether-hexane (1/1)
  4. additionThereto was added 4M HCl-ethyl acetate (1.05 mL)
  5. filtrationthe precipitates were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-617be5223ca14dafa4ffe2639fa7320f
Source dataset
uspto-grants-2011_01
Patent number
US07872006B2

Reaction notes

Loading…