Tributyltin azide → HCID 178497603, compound

Temperature

145 °C

A mixture of azidotributyltin (1.51 mL, 5.48 mmol), and 4-cyano-cyclohexanecarboxylic acid methyl ester (458 mg, 2.74 mmol) in 1,4 dioxane were sealed in a vial and heated in an oil bath at 145° C. for 4 days. The reaction was concentrated, diluted with aqueous sodium bicarbonate (saturated, 200 mL), washed with ethyl acetate (200 mL), acidified to pH 1 with concentrated HCl, and extracted with ethyl acetate (2×200 mL). The organic layer was washed with brine (200 mL), dried over sodium sulfate, concentrated, and tritrated with mixtures of hexanes and ethyl acetate to give 4-(1H-tetrazol-5-yl)-cyclohexanecarboxylic acid methyl ester (304 mg, 52%) as an off white solid. LCMS calcd for C9H14N4O2 (m/e) 210, obsd 211 (M+H).

1. customwere sealed in a vial and
2. concentrationThe reaction was concentrated
3. additiondiluted with aqueous sodium bicarbonate (saturated, 200 mL)
4. washwashed with ethyl acetate (200 mL)
5. extractionextracted with ethyl acetate (2×200 mL)
6. washThe organic layer was washed with brine (200 mL)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated

ORD record

ord-7fc352430d68420a886eef1ed53e63df

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08153644B2