Tert-Butyl nitrite → HCID 59542569, compound

Participants

Reaction Steps

3-(5-Amino-4-ethoxycarbonyl-thiophen-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (1.45 g, 4.1 mmol) was added to a suspension of t-butyl nitrite (6.1 mmol) and copper (II) chloride (4.1 mmol) in IMS (100 mL). The reaction was stirred for 30 minutes. Saturated aqueous ammonium chloride (7 mL) was added and the mixture stirred overnight. The solvent was removed under vacuum and product partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulphate, filtered and the solvent removed. The residue was purified by column chromatography on silica, eluting with 0%-40% ethyl acetate in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound as a pale yellow oil (1.08 g). LCMS m/z 362.20 [M+Na]+ RT=4.30 min (Analytical Method 4).

Provenance & Evidence