Allyl chloroformate → HCID 69677633, compound

To a solution of 4-aminobutanol (630 mg), 5-oxo-2,2-dimethyl-1,3-dioxane (1.0 g) and acetic acid (1.20 ml) in MeOH (9 ml)-DMF (4 ml) was added sodium cyanoborohydride (622 mg) with stirring at ambient temperature, and the mixture was stirred at the same temperature overnight. To the reaction mixture was added dropwise a solution of allyloxycarbonyl chloride (0.97 ml) in THF (2 ml) with stirring under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture were added ethyl acetate (50 ml) and n-hexane (10 ml), and the solution was washed in turn with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (100 ml) eluting with a mixture of n-hexane and ethyl acetate (1:1 v/v). The fractions containing the object compound were collected and evaporated under reduced pressure to give 4-[allyloxycarbonyl-(2,2-dimethyl-1,3-dioxan-5-yl)]aminobutanol (1.04 g).

1. stirringthe mixture was stirred at the same temperature overnight
2. stirringwith stirring under ice-
3. temperaturecooling
4. stirringthe mixture was stirred at the same temperature for 1 hour
5. washthe solution was washed in turn with water and saturated aqueous sodium chloride
6. dry with materialdried over anhydrous magnesium sulfate
7. customevaporated in vacuo
8. customThe resulting residue was chromatographed on silica gel (100 ml)
9. washeluting with a mixture of n-hexane and ethyl acetate (1:1 v/v)
10. additionThe fractions containing the object compound
11. customwere collected
12. customevaporated under reduced pressure

ORD record

ord-fdd2292de30342538c531210dfc59259

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884868B1