Potassium sodium tartarate → HCID 10705537, compound

Temperature

-78 °C

3-t-Butoxycarbonyl-2,2-dimethyl-(4R)-n-hexanoyloxymethyl-4-methyloxazolidine (13.7 g, 39.9 mmol) obtained in Reference example 2(a) was dissolved in dichloromethane (200 ml), and the hexane solution of 1.0M diisobutylaluminium hydride (99 ml, 99.7 mmol) was added dropwise thereto at −78° C. After, the reaction mixture was stirred for 30 minutes at −78° C., cooled down to room temperature, and 10 wt % aqueous potassium sodium tartrate solution (200 ml) was added thereto followed by stirring vigorously for 30 minutes. The reaction solution was extracted with diethyl ether, and after the ether layer was dried over anhydrous sodium sulfate, the solvent was evaporated in vacuo. The residue was purified by flash chromatography on a silica gel column (elution solvent; n-hexane:ethyl acetate=5:2) to afford the title compound (10.5 g, 100% yield) as a white crystalline solid.

1. customat −78° C
2. temperaturecooled down to room temperature
3. stirringby stirring vigorously for 30 minutes
4. extractionThe reaction solution was extracted with diethyl ether
5. dry with materialafter the ether layer was dried over anhydrous sodium sulfate
6. customthe solvent was evaporated in vacuo
7. customThe residue was purified by flash chromatography on a silica gel column (elution solvent; n-hexane:ethyl acetate=5:2)

ORD record

ord-1f3be192869448809c1976926fca4bcb

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06964976B2