Sodium cyanoborohydride → HCID 17912344, compound

Participants

Reaction Steps

The solution of 1,1,1,2,2,3,3-heptafluoro-4-(3-methyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-2-yl)-butan-4-one (0.62 g, 1.6 mmol) in dichloroethane (20 ml) is treated successively with NaCNBH3 (0.42 g, 6.4 mmol) and ZnI2 (0.71 g, 2.24 mmol) and refluxed for 4 days (d). After 2 days, NaCNBH3 (0.42 g, 6.4 mmol) and ZnI2 (0.71 g, 2.24 mmol) are again added. The reaction is observed by means of GC-MS. After 2 days, 40% of the compound employed is reacted, and after 4 days 89%, in addition to a further 11% of starting material. The reaction is then terminated by addition of dilute phoshoric acid (8%, 50 ml). After the evolution of gas has ended, the mixture is extracted with methylene chloride, the organic phase is washed with water (50 ml) and the solvent is stripped off in vacuo after drying over Na2SO4 sicc. The residue (0.65 g, 82.4%, 77% strength according to GC-MS(TIC)) is employed in the subsequent reaction without further purification.

Provenance & Evidence