Potassium Carbonate → (3aR,6aR)-tetrahydrofuro[3,4-d]oxazol-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (3R,4R)-4-aminotetrahydrofuran-3-ol (1.1 g, 7.88 mmol) and DIEA (4.54 ml, 26.0 mmol) in CH2Cl2 (30 mL) was added (bis(trichloromethyl) carbonate (1.75 g, 5.91 mmol) dissolved in CH2Cl2 (5 mL) at RT over a period of 30 min. After stirring for 0.5 h at 25° C., the reaction mixture was added to aqueous K2CO3 solution, stirred for 1 h and the CH2Cl2 was evaporated. The aqueous phase was washed with Et2O and afterwards evaporated to dryness. The residue was triturated with EtOH/THF 1:1, the inorganic salts removed by filtration through a plug of silica gel, and the filtrate was concentrated to provide the title compound as a beige solid (930 mg, 90%): ESI-MS: 147 [M+NH]+.

Provenance & Evidence