Methyl chloroformate → Dimethyl cycloheptane-1,1-dicarboxylate

HRID 2055187Notes

Reaction equation

HRID 2055187 reaction equation
C[C:2]1([C:9]([OH:11])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:12](NC(C)C)(C)C.[Li].[CH3:20][O:21][C:22](Cl)=[O:23]>C1COCC1>[C:2]1([C:9]([O:11][CH3:12])=[O:10])([C:22]([O:21][CH3:20])=[O:23])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 127574891-Methylcycloheptane-1-carboxylic acidHCID 45051747Lithium diisopropylamine

Product 1

HCID 64994993Dimethyl cycloheptane-1,1-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl cycloheptanecarboxylic acid (8.0 g, 51.2 mmol) in THF (18 mL) was added dropwise to a solution of lithium diisopropylamine (8.3 g, 76.8 mmol) in THF (70 mL) at −78° C. After stirring for 1 h at the same temperature, a solution of methylchloroformate (7.26 g, 76.8 mmol) was added slowly and the mixture was allowed to warm to room temperature. After 18 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (100 mL) and was extracted with EtOAc (100 mL×3). The combined organic layers were dried (MgSO4). After removal of the solvent under reduced pressure, purification by flash column chromatography using an eluting system of hexane/EtOAc (95:5) yielded the title compound as a clear, colorless liquid (7.8 g, 71%). MH+215.

Workup

  1. customAfter 18 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (100 mL)
  2. extractionwas extracted with EtOAc (100 mL×3)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customAfter removal of the solvent
  5. customunder reduced pressure, purification by flash column chromatography

Sources & evidence

ORD record
ord-0de9e689a410459281bd4b4e3097cbf2
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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