tert-butyl N-hydroxycarbamate → (1S,4S)-1-(2-Benzyloxy-ethyl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

(2-Cyclohexa-1,3-dienyl-ethoxymethyl)-benzene (9) (6 g, 28 mmol) is dissolved in 280 ml of dry methylene chloride and cooled down to 0° C. After addition of molecular sieves (6 g, UOP Type 4A) and N—BOC-hydroxylamine (5.6 g, 42 mmol) in small portions, tetrapropylammonium(meta)periodate (10.8 g, 28 mmol) is added slowly in small portions the mixture was stirred for 1 h. Then the mixture is diluted with CH2C12 and cooled to −10° C. 2M Na2S2O5 solution is added slowly (exothermic!). The mixture is washed with water, dried over Na2SO4 and evaporated under reduced pressure. The crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), silicagel).

Provenance & Evidence