A Concise, Stereoselective and Scalable Synthesis of Optically Pure (3r,4r)-1-Benzyl- and (3r,4r)-1-Boc-3-Methyl-4-Aminopiperidines

Author:

NIMJE ROSHAN,Hazra Sunit,Kangune Ankit,Pawar Govind,Karmakar Ananta,Pabbisetty Kumar B.,Mortensen Deborah S.,Dodd Dharmpal S.,Li Jianqing,Mathur Arvind,Gupta Anuradha

Publisher

Elsevier BV

Reference32 articles.

1. -Benzyl-3-methylpiperidin-4yl)isoindoline-1,3-dione (100 g, 300 mmol) was taken in a 5 L three neck round bottom flask. MeOH (1600 mL) and DCM (1215 mL) were added followed by addition of hydrazine hydrate (50-60%) (120 mL, 1200 mmol) and the resulting mixture was stirred at rt for 28 h. The reaction mixture was filtered through a celite pad, washed with a mixture of MeOH and DCM (1:1, 3 x 300 mL). The filtrate was concentrated in vacuo. To the crude mass 200 mL water was added, and pH was adjusted to 10 with 10% aqueous NaOH solution. The mixture was extracted with EtOAc (3 x 500 mL);4r 3r;The combined organic layers were washed with water

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