Amine protection Troc group

For a hydrocarbon substrate which does contain tertiary and secondary C—H bonds, a better chemoselectivity is observed with 5 mol% of Rh2[(S)-nttl]4- For instance, a 12 1 ratio is obtained for the C—H amination of adamantane leading to 58% of Troc-protected 1-adamantanamine, compared to 3 1 if Rh2(tpa)4 is used (Scheme 5.9). The protecting group is easy to cleave using Zn in acetic acid and amantadine hydrochloride is then isolated in quantitative yields [77]. 

Troc protecting groups are easy to remove, which is an advantage associated with the use of 2,2,2-trichloroethyl-A/-tosyloxy-carbamate as a nitrene precursor cort5)ared to arylsulfamate, which require harsh reaction conditions to obtain the free amine. Both amantadine (R = H) and memantine (R = Me) hydrochloride were prepared in quantitative yields from the corresponding Troc-protected amino compounds (eq 5). ... 

Acylating agent, reagent for protection of aminoacids with the trichloroethoxycarbonylurethane (troc-urethane) group. Reagent for gc anal, of tertiary amines. Liq. 

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