Cyclohexanecarboxylic acid → HCID 68720952, compound

HRID 657696Notes

Reaction equation

HRID 657696 reaction equation
[CH:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:10][Si:11]([CH3:16])([CH3:15])[CH2:12][CH2:13]O.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH:1]1([C:7]([O:9][CH2:13][CH2:12][Si:11]([CH3:16])([CH3:15])[CH3:10])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 7413Cyclohexanecarboxylic acidHCID 180132-(Trimethylsilyl)ethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 68720952HCID 68720952, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of cyclohexanecarboxylic acid (1.28 g, 10 mmol), 2-(trimethylsilyl)ethanol (1.3 g, 11 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (2.11 g, 11 mmol) in dichloromethane was added 4-dimethylaminopyridine (123 mg, 1.0 mmol). The reaction mixture was stirred at room temperature for 3 d. It was partitioned between ethyl acetate and 2N HCl. The organic phase was washed with brine, saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuuo. The residue was purified by flash chromatograph on silica gel (eluting with 0-20% ethyl acetate in hexane) to provide the title compound as a colorless oil (1.7 g, 75% yield).

Workup

  1. customIt was partitioned between ethyl acetate and 2N HCl
  2. washThe organic phase was washed with brine, saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuuo
  6. customThe residue was purified by flash chromatograph on silica gel (eluting with 0-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-860ae76e132846958994b18ef2681a8a
Source dataset
uspto-grants-2011_12
Patent number
US08076344B2

Reaction notes

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