tert-Butyldimethylsilyl chloride → 3-(Benzyloxycarbonylamino)-1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-cyclobutane

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Reaction Steps

N-(Benzyloxycarbonyl)-3-amino-1-cyclobutanol (2.22 g, 10 mmol) from Step B and t-butyldimethylsilyl chloride (4.8 g, 32 mmol) were combined in 25 mL of anhydrous pyridine and the cloudy suspension was stirred over the weekend at ambient temperature, under a nitrogen atmosphere. After 65 h, the solution was concentrated in vacuo at 35°-40° C. The concentrate was diluted with 250 mL of methylene chloride and the methylene chloride solution was washed with 3×100 mL of water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue (3.9 g) was purified on a 1.0×45 cm silica gel column eluted @5 psi with 100 mL of hexane, followed by 200 mL of 10% acetone in hexane to give 3.16 g (88% yield) of the title compound; MS DCI-NH3M/Z: 336 (M+H)+, 353 (M+NH4)+ ; 1H NMR (CDCl3) δ - 0.03 (s, 6H), 0.83 (s, 9H), 1.75 (m, 2H), 2.68 (m, 2H), 3.69 (m, 1H), 3.93 (m, 1H), 5.06 (s, 2H), 7.30 (m, 5H).

Provenance & Evidence