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

Temperature

25 °C

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]+.

1. stirringstirred for 1 h
2. customthe CH2Cl2 was evaporated
3. washThe aqueous phase was washed with Et2O
4. customafterwards evaporated to dryness
5. customThe residue was triturated with EtOH/THF 1:1
6. customthe inorganic salts removed by filtration through a plug of silica gel
7. concentrationthe filtrate was concentrated

ORD record

ord-65b0fd266c0045739bec8013fcd81e47

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865894B2