Benzyl chloroformate → HCID 57585944, compound

HRID 70268Notes

Reaction equation

HRID 70268 reaction equation
Cl.[CH3:2][C:3]1([CH3:10])[CH2:8][CH2:7][CH2:6][CH:5]([NH2:9])[CH2:4]1.C(N(CC)C(C)C)(C)C.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>C(#N)C>[CH3:2][C:3]1([CH3:10])[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][C:21](=[O:22])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 671599363,3-Dimethylcyclohexan-1-amine hydrochloride

Product 1

HCID 57585944HCID 57585944, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of (3,3-dimethylcyclohexyl)amine hydrochloride (10.0 g, 0.060 mol) and N,N-diisopropylethylamine (15.8 g, 0.12 mol) in acetonitrile (125 mL) at ice bath temperature was added a solution of benzyl chloroformate (11.4 g, 0.067 mol) in acetonitrile (25 mL), dropwise. The mixture was stirred overnight, gradually warming to ambient temperature, and concentrated in vacuo. The residue was partitioned between ethyl acetate/5% citric acid solution and the layers were separated. The organic layer was washed with brine, dried over Na2SO4, adsorbed onto silica gel and purified by flash chromatography (CH2Cl2/hexanes) affording the title compound as a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ ppm: 0.85 (s, 6H), 0.92-1.02 (m, 3 H), 1.25 (d, 1 H), 1.36-1.52 (m, 3 H), 1.76 (br. d, 1 H), 3.36-3.44 (m, 1 H), 4.96 (s, 2H), 7.10 (d, 1 H), 7.27-7.36 (m, 5H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate/5% citric acid solution
  3. customthe layers were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. custompurified by flash chromatography (CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-83501960d07c4872926e2fb37b3e71e7
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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