Tetrabutylammonium Fluoride → HCID 59135184, compound

Participants

Reaction Conditions

Reaction Steps

Tetrabutylammonium fluoride (1M, in THF, 177 μL, 0.177 mmol) was added dropwise to a stirred solution of 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 (2:1 mixture of regioisomers, 65.2 mg, 0.161 mmol) in THF (2 mL) at 0° C. The reaction was stirred for 2 h at 0° C., diluted with saturated NH4Cl (10 mL) and extracted with EtOAc (3×30 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-80% EtOAc in hexanes gradient) to afford benzyl [(1S,2S)-2-hydroxy-1-methyl-2-(2-methyl-2H-tetrazol-5-yl)ethyl]carbamate and benzyl [(1S,2S)-2-hydroxy-1-methyl-2-(1-methyl-1H-tetrazol-5-yl)ethyl]carbamate. 2-methyl isomer (INTERMEDIATE 20): LCMS calc.=292.1; found=292.1 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 7.33-7.29 (m, 5H), 5.59 (d, J=8.5 Hz, 1H), 5.09-5.00 (m, 5H), 4.49 (m, 1H), 4.26 (s, 3H), 1.07 (d, J=6.9 Hz, 3H). 1-methyl isomer (INTERMEDIATE 19): LCMS calc.=292.1; found=292.1 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 7.33-7.29 (m, 5H), 5.72 (s, 1H), 5.07 (m, 3H), 4.99 (m, 2H), 4.18 (m, 1H), 4.10 (s, 3H), 1.24 (d, J=6.7 Hz, 3H).

Provenance & Evidence