Sodium Hydroxide → (1R,2S)-2-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

Temperature

30 °C

Into a 2-L jacketed vessel set at 30° C. was placed dimethyl cyclohexane-1,2-dicarboxylate (2, 84.6 g, 0.42 mol) and 900 mL of 0.1M potassium phosphate buffer, pH 8. The mixture was continuously stirred at 30° C. and PLE (600 mg, 10200 units) was added. The mixture was stirred for 91 hours and the pH was maintained at 8 by addition of 5M NaOH solution. An aliquot from the mixture was analyzed by GC to confirm that residual starting material was less than 5%. The reaction mixture was then filtered through a Celite™ bed and the filtrate was extracted with 250 mL MTBE to remove residual starting material. The aqueous phase was then acidified to pH 4 with concentrated HCl and extracted with 3×500 mL MTBE. The combined extracts were dried over magnesium sulfate and solvent was removed under reduced pressure, to yield 69.28 g (88% yield) of (1R,2S)-2-(methoxycarbonyl)cyclohexane carboxylic acid (4) as a colorless oil with e.e.=79%.

1. customInto a 2-L jacketed vessel set at 30° C.
2. additionPLE (600 mg, 10200 units) was added
3. stirringThe mixture was stirred for 91 hours
4. filtrationThe reaction mixture was then filtered through a Celite™ bed
5. extractionthe filtrate was extracted with 250 mL MTBE
6. customto remove residual
7. extractionextracted with 3×500 mL MTBE
8. dry with materialThe combined extracts were dried over magnesium sulfate and solvent
9. customwas removed under reduced pressure

ORD record

ord-cf73ef5fa310406b9d64a8cb87da0669

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09080193B2