Sodium hydride → 3-Bromo-1-t-butoxycarbonylmethylperhydroazonin-2-one

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Reaction Steps

Add a solution of 7.35 g. 3-bromoperhydroazonin-2-one [Nagasawa et al., J. Med. Chem., 14, 501 (1971)]and 8.47 g t-butyl iodoacetate in 70 ml THF to a suspension of 0.881 g sodium hydride in 35 ml THF. After 2 hours at room temperature, add 15 ml saturated NH4Cl solution, filter and concentrate the filtrate in vacuo. Partition the residue between ether and H2O and wash the organic phase with H2O and brine. Dry the ether solution and filter. Decolorize the filtrate with charcoal, filter and concentrate the filtrate in vacuo to isolate 3-bromo-1-t-butoxycarbonylmethylperhydroazonin-2-one. Purify a sample for characterization by silica gel chromatography. Anal. C14H24BrNO3). Calc: C, 50.31; H, 7.24; N, 4.18; Br, 23.91. Found: C, 49.86; H, 7.33; N, 4.30; Br, 23.51. Mass spectrum: M+ at 334; m/e: 278 (M+ --C 4 H8); 261 (M+ --C4H9O); 232 (M+ --C4H9CO2 --H, base).

Provenance & Evidence