Reacción #2383812

Ecuación de reacción

sodium bicarbonate

hydrogen peroxide

product

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

Borane

→

title compound

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

Disolventes

Methanol

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   Otroresulting in a white precipitate
3. 3
   FiltraciónThe precipitate was filtered off
4. 4
   Otrothe solvent was removed from the filtrate under reduced pressure

Procedimiento

A solution of the product of Example 6 (3.0 g, 0.0155 mol) in tetrahydrofuran (44 mL) under nitrogen was treated with a Borane.THF complex (1M, 18.56 mL) and this reaction was stirred for 2 hours. Methanol (2.50 mL) was added before a solution of saturated sodium bicarbonate (2.32 mL) and hydrogen peroxide (30%, 2.32 mL) were added resulting in a white precipitate. The precipitate was filtered off and the solvent was removed from the filtrate under reduced pressure to afford the title compound. 1H NMR (CDCl3, 300 MHz) d 1.2-2.5 (m, 8H), 2.59 (m, 2H), 2.95 (dd, 2H), 3.72 (m, 2H), 4.25 (m, 1H). 13C NMR (CDCl3, 75 MHz) d 23.87, 25.73, 26.23, 28.57, 31.88, 53.97, 61.90, 68.07, 159.9, 160.8.

Fuente