NaBH4 – a novel method for the deprotection of Nω-nitro-arginine

Sebestyén, Mónika and Kóczán, György and Csámpai, Antal and Hudecz, Ferenc (2016) NaBH4 – a novel method for the deprotection of Nω-nitro-arginine. TETRAHEDRON LETTERS, 57. pp. 546-548. ISSN 0040-4039

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Abstract

The selective deprotection of Nω-nitro-arginine derivatives represents a major preparative challenge. This problem can be circumvented by the use of catalytic hydrogenation, but often high pressure, elevated temperature, and/or long reaction times are needed. In certain cases hydrogenation is not suitable, for example, small-scale reactions, parallel synthesis, or due to selectivity issues. Herein, we demonstrate for the first time, the use of NaBH4 in the presence of a metal ion catalyst for the removal of the Nω-nitro moiety under simple, ‘open-vessel’ conditions. This process using NaBH4 does not remove the benzyloxy-carbonyl-protecting group; thus the method is orthogonal for this protecting scheme.

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