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

Participants

Reaction Conditions

Reaction Steps

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%.

Provenance & Evidence