Ethyl Acetate → 3-t-Butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-oxazol-2-yl)azetidine

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidine (4.95 g, 11.3 mmol) (obtained as described in Reference Example 70(8)) in anhydrous tetrahydrofuran (100 ml) was added dropwise a suspension of lithium aluminium hydride (1.29 g, 33.9 mmol) in anhydrous tetrahydrofuran (250 ml) in an ice bath under an atmosphere of nitrogen and the mixture was stirred in an ice bath for 5 minutes. After checking the completion of the reaction, magnesium sulfate decahydrate was gradually added to the reaction mixture in an ice bath. After termination of foaming, the resulting mixture was stirred at room temperature for 1 hour. Ethyl acetate was gradually added to the reaction mixture. The resulting mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene:acetonitrile (3:1) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-oxazol-2-yl)azetidine (3.88 g, yield 84%) as a white solid.

1. additionwas gradually added to the reaction mixture in an ice bath
2. stirringAfter termination of foaming, the resulting mixture was stirred at room temperature for 1 hour
3. customThe resulting mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-24b786e4e475460abc88f001f1eba708

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001897B2