Réaction #2368012

Équation de réaction

4-methoxybicyclo[2.2.2]octane-1-carboxylic acid

DIEA

diphenyl phosphoryl azide

phenylmethanol

→

desired product

Rendement 96.0%

Benzyl(4-methoxybicyclo[2.2.2]octan-1-yl)carbamate

Rendement 96.0%

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated
2. 2
   AutreThe residue was purified by silica gel column chromatography (5% methanol in DCM)

Mode opératoire

To a solution of 4-methoxybicyclo[2.2.2]octane-1-carboxylic acid (5.9 g, 32 mmol) in dioxane (80 mL) was added DIEA (8.3 g, 64.2 mmol), diphenyl phosphoryl azide (13.2 g, 48 mmol) and phenylmethanol (17.3 g, 160 mmol). The mixture was stirred at 80° C. overnight and then concentrated under reduce pressure. The residue was purified by silica gel column chromatography (5% methanol in DCM) to give the desired product. (9 g, 31 mmol, yield 96%). MS (ESI) m/z=290.2 [M+H]+.

Source