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

A solution of 3-t-butyldiphenylsilyloxy-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)azetidine (5.0 g, 10.7 mmol) (obtained as described in Reference Example 2(1)) in anhydrous tetrahydrofuran (100 ml) was added dropwise to a solution of lithium aluminum hydride (1.22 g, 32.1 mmol) in anhydrous tetrahydrofuran (250 ml) in an ice bath under an atmosphere of nitrogen and the mixture was stirred for 1.5 hours under the same conditions. 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 n-hexane:ethyl acetate (3:1→1:2) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine (3.88 g, yield 86%) 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 기록

ord-014041af956b44af8dbbac4fa2820769

출처 데이터셋

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07001897B2