2-OXABICYCLO[3.1.0]HEXANE-6-CARBOXYLIC ACID synthesis

Yield:99418-15-2 60.9%

Reaction Conditions:

with water;lithium hydroxide in tetrahydrofuran;methanol;

Steps:

To a stirred solution of ethyl 2-oxabicyclo [3.1.0] hexane-6-carboxylate (0.4 g, 2.56 mmol) in MeOH/THF/H20 (2 mL/2mL/2 mL) was added LiOH (0.307 g, 12.81 mmol) and the resulting mixture was stirred for 12h at 25°C. Solvent was evaporated under reduced pressure and the residue was dissolved in water (20 mL) and pH wasadjusted to 6 with iN HC1 solution. Acquous layer was extracted with dichloromethane (3x50 mL), dried over sodium sulfate and evaporated under reduced pressure to give 2-oxabicyclo [3.1.0] hexane-6-carboxylic acid (0.2 g, 1.56 1 mmol, 60.9 % yield).

References:

WO2015/5901,2015,A1 Location in patent:Page/Page column 721; 722