Sodium Carbonate → (2-Acetyl-cyclohexyl)-carbamic acid benzyl ester

HRID 1593989Notes

Reaction equation

HRID 1593989 reaction equation
Br.[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[C:9]([O:11]CC)=O.Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].[C:25](=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH2:18]([O:17][C:15](=[O:16])[NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[C:9](=[O:11])[CH3:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 122236269Ethyl (1R,2S)-2-aminocyclohexane-1-carboxylate hydrobromide

Product 1

HCID 20732580(2-Acetyl-cyclohexyl)-carbamic acid benzyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of ethyl cis-2-amino-1-cyclohexanecarboxylate HBr salt (22.34 g, 88.6 mmol) in 250 mL of methylene chloride, was added benzyl chloroformate (12.6 mL, 88.3 mmol) and 250 mL of an aqueous sodium carbonate solution. The reaction mixture was stirred for 24 h at ambient temperature. The organic layer was separated and washed with 250 mL of water, dried over sodium sulfate, filtered and concentrated to give a crude liquid. The product was purified by column chromatography (10-50:90-50 ethyl acetate/hexanes) to give 26.45 g of (2-acetyl-cyclohexyl)-carbamic acid benzyl ester as a clear liquid. Yield: 98%, MS: 306 (M+H+).

Workup

  1. customThe organic layer was separated
  2. washwashed with 250 mL of water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude liquid
  7. customThe product was purified by column chromatography (10-50:90-50 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2ff250ba1c11443fb3c0cf81a0f0bb1e
Source dataset
uspto-grants-2007_11
Patent number
US07300934B2

Reaction notes

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