Benzyl Alcohol → (8-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamic acid benzyl ester

Participants

Reaction Conditions

Reaction Steps

Dissolve 8-methyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid (Chem. Pharm. Bull., 1984, 32(6), 2267-2278) (10.9 g, 54.4 mmol) in benzene (500 mL). Add triethylamine (6.61 g, 65.32 mmol), diphenylphosphoryl azide (16.48 g, 59.88 mmol), and benzyl alcohol (8.83 g, 81.66 mmol) under nitrogen. Stir and heat the reaction mixture to 80° C. Continue to heat the reaction at 80° C. for 8 hours, then cool to room temperature. Add water (500 mL), and extract the aqueous layer with ethyl acetate (3×500 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 5-25% of EtOAc/Hexane) to give 13.45 g (81%) of (8-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamic acid benzyl ester as a colorless oil.

Provenance & Evidence