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25th March 2013 @ 05:50

Performed concurrently with AT-5-5.

 

To AT-5 (2.10 g, 12.3 mmol, 1.0 equiv.) in THF (120 mL) at -78 C was added n-BuLi (7.38 mL, 18.5 mmol, 1.5 equiv.) dropwise and the reaction mixture stirred at -78 C for 30 minutes. Bromine (1.26 mL, 24.6 mmol, 2.0 equiv.) was added dropwise and the reaction mixture warmed to rt and stirred for 1 h. 

The reaction mixture was diluted with an aqueous solution of sodium thiosulfate (150 mL) and extracted into ethyl acetate (3 x 100 mL). The combined organic extracts were dried (MgSO4), concentrated under reduced pressure and the residue purified by flash column chromatography (7:1 hexanes:ethyl acetate) to give starting material AT-1 (0.115 g, 5%) and product AT-5 (1.86 g, 64% based on RSM).

 

HIRAC

AT-5-1.pdf
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AT-5-1.pdf
AT-5-6.jpg