Pyridine → Carbonic acid 1-chloroethyl ester (1R,2R)-2-methylcyclohexyl ester

HRID 2089646Notes

Reaction equation

HRID 2089646 reaction equation
Cl[C:2]([O:4][CH:5]([Cl:7])[CH3:6])=[O:3].CC1(C)[C:13]2([CH2:17]S(O)(=O)=O)[C:14]([CH2:16][CH:10]1[CH2:11][CH2:12]2)=[O:15].N1C=CC=CC=1.C[C@@H]1CCCC[C@H]1O>C1COCC1.CCCCCCC.C(OCC)(=O)C>[CH3:17][C@@H:13]1[CH2:12][CH2:11][CH2:10][CH2:16][C@H:14]1[O:15][C:2](=[O:3])[O:4][CH:5]([Cl:7])[CH3:6]

Participants

8

Reactant 4

HCID 1049PyridineHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-2×HCID 24004trans-2-MethylcyclohexanolHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 68212867Carbonic acid 1-chloroethyl ester (1R,2R)-2-methylcyclohexyl ester

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

To a mixture of 1-chloroethyl chloroformate [CSA No. 50893-53-3] (0.416 mL), pyridine (0.624 mL), and THF (25 mL), (1R,2R)-2-methylcyclohexanol [CSA No. 19043-03-9] (441 mg) dissolved in THF (5 mL) was added at −78° C. After stirring the mixture overnight at room temperature, ethyl acetate (100 mL) and heptane (100 mL) were added to the mixture. The resulting mixture was sequentially washed with 0.5 N hydrochloric acid (50 mL), saturated aqueous sodium hydrogen carbonate solution (50 mL), water (50 mL), and saturated aqueous sodium chloride solution (50 mL), and dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and the filtrate obtained was concentrated under reduced pressure to obtain the captioned compound (482 mg).

Workup

  1. additionwas added at −78° C
  2. washThe resulting mixture was sequentially washed with 0.5 N hydrochloric acid (50 mL), saturated aqueous sodium hydrogen carbonate solution (50 mL), water (50 mL), and saturated aqueous sodium chloride solution (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe resulting mixture was filtered
  5. customthe filtrate obtained
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-87eccb2d1671482eaca09ac69578aa9c
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

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