Methyl chloroformate → HCID 45095662, compound

A solution of 4-ethyl-cyclohexanecarboxylic acid methyl ester (10.4 g, 61.2 mmol) in THF (25 mL) was added dropwise to a solution of lithium diisopropylamine (11.2 g, 92 mmol) in THF (90 mL) at −78° C. After stirring for 1 h at the same temperature, a solution of methylchloroformate (8.7 g, 92 mmol) in THF (25 mL) 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 (150 mL). THF was removed in vacuo and the aqueous residue was extracted with EtOAc (200 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 colorless liquid (14 g) with diisopropyl-carbamic acid methyl ester present. MH+229.

1. customAfter 18 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (150 mL)
2. customTHF was removed in vacuo
3. extractionthe aqueous residue was extracted with EtOAc (200 mL×3)
4. dry with materialThe combined organic layers were dried (MgSO4)
5. customAfter removal of the solvent
6. customunder reduced pressure, purification by flash column chromatography

ORD record

ord-4039eddd777840f8978f219032b73cbe

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07332485B2