Indinavir – An Summary

The synthesis of the piperazine constructing block of indinavir using a extra convergent, environment friendly, and greener method that utilized asymmetric catalysis as an alternative of a decision for the important thing intermediate 4.4.7, is shown in Scheme 12. An Ugi multicomponent reaction provided intermediate 4.4.16, which without isolation was treated with triethylamine to undergo elimination of HCl to afford 4.4.17. Cyclization of 4.4.17 to 4.4.18 was achieved in 60% yield by rigorously monitoring the reaction situations and the subsequent key asymmetric hydrogenation was achieved with 7 mol% Rh-BINAP in methanol to provide 4.4.19 in quantitative yield and 97% ee.40 Removal of the formyl group with 35% aqueous hydrazine gave 4.4.7 in good yield with out racemization. Scheme 12. Synthesis of the piperazine portion (4.4.7) of indinavir (Crixivan). Reagents and panadol generic conditions: biaxin generic (a) Et3N; (b) t-BuOK; (c) 7 mol% Rh-BINAP, H2 (100 atm), MeOH, forty °C; (d) 35% aqueous hydrazine. The synthesis of the epoxide constructing block 4.4.23 is proven in Scheme 13.41 Intermediate 4.4.21 was obtained in two chemical steps from cis-1-amino-indanol (4.4.20)forty two after which alkylated with allyl bromide to afford 4.4.22 in a 96:Four ratio. Scheme 13. Greener indinavir approach: Synthesis of intermediate 4.4.23. Reagents and circumstances: (a) Ref. 42; (b) LHMDS, thorazine allyl bromide, buy voltaren sr THF, −15 °C; (c) (i) NCS, NaI, IPAc, aqueous NaHCO3; (ii) NaOMe, THF. Scheme 14. Convergent synthesis of indinavir (Crixivan). Reagents and conditions: (a) IPA, 6 N HCl, reflux; (b) 3-picolyl chloride.

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