Stannous Chloride → cis-(6-Benzhydryl-tetrahydropyran-3-yl)-(4-amino-benzyl)-amine

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Reaction Steps

A mixture of cis-(6-benzhydryl-tetrahydropyran-3-yl)-(4-nitro-benzyl)-amine (160 (0.16 g, 0.39 mmol) and SnCl2/2H2O (0.35 g, 1.55 mmol) in EtOH/EtOAc (20 ml, 7:3) was heated to reflux for 1.5 h (monitored by TLC, Hex/EtOAc/Et3N 5:5:0.4). After removal of the solvent, the residue was diluted with 10% NaHCO3 and EtOAc and stirred vigorously for 30 min. After filtration the organic phase was separated and the aqueous phase was extracted with EtOAc (20 ml×2). The combined organic phase was dried over Na2SO4. After removal of the solvent, flash chromatography gave 16o, cis-(6-benzhydryl-tetrahydropyran-3-yl)-(4-amino-benzyl)-amine (0.087 g, 60%).

Provenance & Evidence