Cyclohexanemethanol → HCID 67384630, compound

HRID 2360970Notes

Reaction equation

HRID 2360970 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:17]1([CH2:23]O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:20]1[CH2:21][CH2:22][CH:17]([CH2:23][O:15][C:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)=[O:16])[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 7507CyclohexanemethanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 67384630HCID 67384630, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (66.94 mmol; 15.35 g) in dichloromethane (100 mL) was added cyclohexylmethanol (55.79 mmol; 6.37 g), dimethylaminopyridine (1.12 mmol; 0.14 g) and dicyclohexylcarbodiimide (66.94 mmol; 12.83 g) and the resulting mixture was stirred for 3 hours at room temperature. The resulting solution was evaporated and the residue was dissolved in ethyl acetate (200 mL). The resulting solution was washed with a 1N hydrochloric acid solution (2×50 mL) and brine (50 mL), and dried over magnesium sulfate. After filtration and evaporation, the residue was purified via flash column chromatography ((eluent gradient: 0 to 5% EtOAc in heptane) to yield piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-cyclohexylmethyl ester after evaporation. MS (ESI) m/z 326.29 [M+H]+.

Workup

  1. customThe resulting solution was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. washThe resulting solution was washed with a 1N hydrochloric acid solution (2×50 mL) and brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration and evaporation
  6. customthe residue was purified via flash column chromatography ((eluent gradient: 0 to 5% EtOAc in heptane)

Sources & evidence

ORD record
ord-ae4d56e9af7740ef900cbb0516a07bda
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

Loading…