Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-tert-butoxycarbonylaminopropionate

Participants

Reaction Conditions

Reaction Steps

A solution of 10.9 g (65.4 mmol) of (1-hydroxymethyl)adamantane and 10.6 g (65.4 mmol) of carbonyldiimidazole in 60 ml of THF is stirred at 50° C. for 1.5 h. 9.7 g (32.7 mmol) of (13.9) in 25 ml of THF and 5.6 ml (32.7 mmol) of diisopropylethylamine (DIPEA) are added and the mixture is stirred at 60° C. for 4 h and then left to stand at room temperature overnight. The solvent is removed in vacuo and the residue is chromatographed through silica gel using heptane/ethyl acetate=7/3. 8.7 9 (59%) of (13.10) are obtained as a colorless oil.

Provenance & Evidence