The plethora of protecting groups for basic nitrogen which can be found in the literature attest to the importance of this aspect of amine chemistry.1 While interesting and clever new choices continue to appear on a quite frequent basis,2 the field is nonetheless essentially dominated by use of the Boc,3 Cbz,4 and Fmoc5 moieties, presumably owing to their proven service. Unlike protecting group chemistry of alcohols, which is heavily weighted toward silicon, relatively few amine derivatives are available which take advantage of a chemospecific fluoride-mediated unmasking. The hydrolytic lability of silylated amines (e.g., sta-base)6 has encouraged use of heartier carbamate (e.g., Teoc; C(O)OCH2CH2SiMe3) and sulfonamide (e.g., SES; SO2CH2CH2TMS) residues. However, these are rather expensive and require steps for precursor preparation. Moreover, while deprotection of Teoc is oftentimes effected by mild fluoride ion, a SES derivative requires CsF in refluxing CH3CN. Noticeably absent from this repertoire is the direct preparation9 of a stable protecting group analogous to Boc, Cbz, and Fmoc (i.e., a carbamate) which contains a readily available trisubstituted silicon atom attached directly to oxygen (Figure 1). In this report we describe the triisopropylsilyloxycarbonyl moiety (i.e., the Tsoc group) as a novel, easily formed, and isolable carbamate protecting group for primary and secondary amines. Protection. N-Tsoc derivatives are easily fashioned by initially treating the amine dissolved in DMF or CH2Cl2 containing Et3N (1-3 equiv) at -78 °C with dry CO2 gas or with crushed dry ice. After ca. 30-60 min, the mixture containing the carbamic acid salt 1 is treated with TIPS-OTf (1 equiv).10 Warming to room temperature followed by a standard aqueous extractive workup and chromatography on SiO2 affords the protected material (Scheme 1). Several illustrative examples can be found in Table 1. Yields tend to be good in most cases. Notably, hydroxyl group protection is not necessary (entries 2, 8, and 9). While less basic anilines lead to the anticipated carbamates, anilines which are further deactivated by attachment of an electronwithdrawing group (entry 7) did not go to completion. Other silyl carbamates, such as that formed using t-BuPh2SiCl (to give 2, Scheme 2), can also be isolated, an alternative should