Reacción #2383811

Ecuación de reacción

methanol

product

6,7,8,9-tetrahydro-3-oxo-3H,5H-[1,2,4]oxadiazolo[4,3-a]azepine-5-acetaldehyde

borane

→

title material

Rendimiento 70.6%

6,7,8,9-tetrahydro-5-(2-hydroxyethyl)-3H,5H-[1,2,4]oxadiazolo[4,3-a]azepin-3-one

Rendimiento 70.6%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   OtroThe solvent was removed under reduced pressure
3. 3
   SecadoThe organic layer was dried over magnesium sulfate
4. 4
   Otroall solvent was removed under reduced pressure
5. 5
   OtroThe residue was chromatographed
6. 6
   Lavadoeluting with 1:1 ethyl acetate/hexane

Procedimiento

To a solution of the product of Example 8 (3.0 g, 0.015 mol) in tetrahydrofuran (20 mL) was added a borane. THF complex (20 mL, 0.020 mol). The reaction stirred for 2 hours upon which methanol (19 mL) was added. The solvent was removed under reduced pressure. The resulting oil was partioned between CH2Cl2 (40 mL) and water (2×20 mL). The organic layer was dried over magnesium sulfate and all solvent was removed under reduced pressure. The residue was chromatographed eluting with 1:1 ethyl acetate/hexane to produce 2.1 g (69%) of the title material. 1H NMR (CDCl3, 300 MHz) d 1.18-2.15(m, 8H), 3.59(m, 2H), 4.39(m, 1H). 13C NMR (CDCl3, 75 MHz) d 24.45, 25.71, 26.47, 32.56, 34.67, 51.16, 58.85, 160.66, 160.89.

Fuente