Imidazole → (3aR,4S,5R,6aS)-4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-5-[(oxan-2-yl)oxy]hexahydro-2H-cyclopenta[b]furan-2-one

To an anhydrous N,N-dimethylformamide (125 mL) solution of (3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one (CAS registry number: 69222-61-3) (47.5 g) and imidazole (16.3 g) was added dropwise an anhydrous N,N-dimethylformamide (82.5 mL) solution of t-butyldimethylsilyl chloride (30.5 g) in a cold-water bath. The mixture was raised to room temperature and stirred for 2 hours, ethanol (1.25 mL) was then added to the reaction mixture, and the mixture was further stirred for 1 hour. The reaction mixture was poured into ice water (500 mL), hexane (200 mL) and ethyl acetate (100 mL) were added thereto, and the mixture was stirred. The two layers were separated, the organic layer was washed with 1 M hydrochloric acid (100 mL), water (100 mL×two times), a saturated aqueous sodium bicarbonate solution (100 mL) and a saturated saline (100 mL), dried with anhydrous sodium sulfate, and concentrated to obtain a titled compound (68.4 g) having the following physical property values.

1. stirringthe mixture was further stirred for 1 hour
2. additionwere added
3. stirringthe mixture was stirred
4. customThe two layers were separated
5. washthe organic layer was washed with 1 M hydrochloric acid (100 mL), water (100 mL×two times)
6. dry with materiala saturated aqueous sodium bicarbonate solution (100 mL) and a saturated saline (100 mL), dried with anhydrous sodium sulfate
7. concentrationconcentrated

ORD record

ord-55d752f9356a485fb51eb991ef37f047

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150537B2