Methyl iodide → (1s,4s)-4-(Methoxycarbonyl)-4-methylcyclohexane-1-carboxylic acid

Temperature

-78 °C

N,N-Diisopropylamine (1.18 mL, 8.35 mmol) was added dropwise to a 2M solution of nbuthyllithium (4.188 mL, 8.4 mmol) at −78° C. under nitrogen. After 15 min at this temperature the solution was raised to and held at 0° C. for 15 min prior to re-cooling to −78° C. and treatment with a solution of 4-(methoxycarbonyl)cyclohexanecarboxylic acid (0.62 g, 3.34 mmol) in THF (8 mL). After 30 min., iodomethane (0.31 mL, 5 mmol) was added dropwise and the mixture was allowed to warm to rt over 2 hr. The mixture was cooled to at 0° C., quenched with 2 N HCl (10 mL) then was extracted with EtOAc (2×10 mL), washed with brine (3×15 mL), and dried over anhydrous magnesium sulfate. Concentration of the combined organic extracts afforded a yellow solid. NMR (CDCl3) consistent with crude, desired product.

1. temperatureAfter 15 min at this temperature the solution was raised to and
2. waitAfter 30 min.
3. temperatureto warm to rt over 2 hr
4. temperatureThe mixture was cooled to at 0° C.
5. customquenched with 2 N HCl (10 mL)
6. extractionthen was extracted with EtOAc (2×10 mL)
7. washwashed with brine (3×15 mL)
8. dry with materialdried over anhydrous magnesium sulfate
9. customConcentration of the combined organic extracts afforded a yellow solid

ORD record

ord-e93c291e5cc64446bf87558c7b22e366

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700594B2