benzhydryl (E)-(2S,3S,5R)-3-(2-formyl-vinyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate → benzhydryl (E)-(2S,3S,5R)-3-(3-hydroxy-propenyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

5.80 g (14.2 mmol) of benzhydryl (E)-(2S,3S,5R)-3-(2-formyl- vinyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 240 ml of toluene under argon and cooled to 0° C. Then, 14.2 ml (21.3 mmol) of a 20% diisobutyl-aluminium hydride solution (in toluene) were added dropwise and the cooling bath is removed. The reaction mixture was stirred at room temperature for 6 hours, poured into 150 ml of saturated ammonium chloride solution and extracted three times with 200 ml of methylene chloride each time. The combined organic extracts were washed once with 300 ml of water as well as saturated sodium chloride solution, dried over magnesium sulfate, filtered and freed from solvent on a rotary evaporator. The residual yellow oil was chromatographed over silica gel (particle size 0.040-0.063 mm) with ethyl acetate:n-hexane (9:16) as the eluent. Yield: 1.90 g (32%) of colorless resin IR (film): 3480(br), 1778, 1750, 1202, 1080, 988 cm-1MS: (M+NH4)+ 427.6

Provenance & Evidence