Trimethylsilyldiazomethane → HCID 86603426, compound

Participants

Reaction Steps

(Trimethylsilyl)diazomethane (2M in hexanes, 459 μL, 0.918 mmol) was added dropwise to a solution of the crude benzyl [(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methyl-2-(1H-tetrazol-5-yl)ethyl]carbamate and benzyl [(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methyl-2-(2H-tetrazol-5-yl)ethyl]carbamate in CH2Cl2/MeOH (3:2, 5 mL) at room temperature under N2. After 15 min and gas evolution had ceased, the reaction mixture was concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-70% EtOAc in hexanes gradient) to afford benzyl [(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methyl-2-(1-methyl-1H-tetrazol-5-yl)ethyl]carbamate and benzyl [(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methyl-2-(2-methyl-2H-tetrazol-5-yl)ethyl]carbamate, as a 2:1 mixture of regioisomers. LCMS calc.=406.2; found=406.2 (M+1)+.

Provenance & Evidence