A Multikilogram-Scale Synthesis of (R)-Methyl 2-[(1r, 4R)-4-(tert-Butoxycarbonylamino) cyclohexyl]-2-(2-nitrophenylsulfonamido) acetate-A Doubly Protected Building …

G Carr, S Butterworth, P Walker, F Reck, B Geng…

Index: Carr, Gregory; Butterworth, Sam; Walker, Phil; Reck, Folkert; Geng, Bolin; Pandarinathan, Lakshmipathi Synthesis, 2012 , vol. 44, # 6 p. 875 - 880

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Abstract

Abstract A robust and scalable synthesis of (R)-methyl 2-[(1r, 4R)-4-(tert- butoxycarbonylamino) cyclohexyl]-2-(2-nitrophenylsulfonamido) acetate is reported. This serves as a scaffold for the preparation of trans-substituted aminocyclohexanes. The key synthetic step is the reduction of d-4-hydroxyphenylglycine, or a protected equivalent, to achieve the required regiochemistry across the cyclohexyl ring.