Toluene → ((1S,2S,4S)-2-Hydroxy-4-hydroxymethyl-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester

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Reaction Steps

A solution of 1.0 g of the pyrrolidine 8 in 2.5 mL of tetrahydrofuran is added to a mixture of 0.37 g of sodium in 5 mL of ammonia and 2.5 mL of tetrahydrofuran at −50° C. The mixture is stirred for 3 h then 2.56 g of ammonium chloride is added and the mixture allowed to warm to r.t. To the mixture is then added 40 mL of toluene, 1.9 g of acetic acid and 25 mL of water. The phases are separated and the aqueous phase is back-extracted with 25 mL of toluene. The combined organic phases are then washed with 4×120 mL of 1:1 water-brine, dried over sodium sulfate and the solvent removed in vacuum, affording e.g. 0.76 g of the product 9a as an oil.

Provenance & Evidence