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

N,N-Diisopropylamine (1.18 mL, 8.35 mmol) was added dropwise to a 2M solution of n butyllithium (4.18 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-cooloing 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. customto re-cooloing to −78° C.
3. waitAfter 30 min.
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-b720fe5e37d647f48fa53bd729c1844a

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943767B2