Diethylamine → HCID 178465145, compound

A stirred and cooled (0° C.) solution of trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (0.500 g, 2.69 mmol) in CH2Cl2 (10 mL) was treated dropwise with a solution of oxalyl chloride (2.0 M in CH2Cl2 1.58 mL, 3.15 mmol) and one drop of DMF, under an atmosphere of nitrogen. The reaction was stirred for 20 min at 0° C., allowed to warm to room temperature and stirred for an additional 2 h. The product was placed under high vacuo for 20 min, dissolved in THF (15 mL) and treated with diethylamine (2.0 M solution in THF, 1.37 mL, 2.73 mmol) and triethylamine (380 uL, 2.73 mmol). The reaction was stirred at room temperature for an additional 18 h. Saturated NH4Cl (1 mL) was added and the resultant mixture was partitioned between H2O (20 mL) and EtOAC (20 mL). The aqueous layer was re-extracted with EtOAc (3×20 mL) and the combined extracts were washed with brine (40 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient) to afford methyl trans-4-[(ethylamino)carbonyl]cyclohexanecarboxylate as a colorless oil. LCMS=214.2 (M+1)+.

1. stirringThe reaction was stirred for 20 min at 0° C.
2. stirringstirred for an additional 2 h
3. stirringThe reaction was stirred at room temperature for an additional 18 h
4. customthe resultant mixture was partitioned between H2O (20 mL) and EtOAC (20 mL)
5. extractionThe aqueous layer was re-extracted with EtOAc (3×20 mL)
6. washthe combined extracts were washed with brine (40 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient)

ORD record

ord-1680118ddb414d6db13b8758ee1801ba

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07781426B2