反应详情

To a solution of tert-butyl diallylcarbamate (0.63 g, 3.2 mmol) in DCM at −78° C. was bubbled ozone until a blue color persisted. Nitrogen was bubbled through the reaction to remove excess ozone, followed by addition of a DCM solution of (6S)-6-amino-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (0.14 g, 0.80 mmol) and triethylamine (0.22 mL, 1.6 mmol). Then NaB(OAc)3H (0.85 g, 4.0 mmol) was added to the reaction. The mixture was allowed to warm to RT and stir overnight. LC showed formation of the desired product, which was separated by prep-TLC to furnish 87 mg of tert-butyl 4-[(2S)-6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl]piperazine-1-carboxylate. LC-MS (IE, m/z): 173 [M+1]+. The material was further treated with TFA to afford crude (6S)-6-piperazin-1-yl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile.

1. customNitrogen was bubbled through the reaction
2. customto remove excess ozone