4-Tert-butylbenzene-1,2-diamine → HCID 86699083, compound

Participants

Reaction Steps

(2S,3R)-1-(tert-Butyldimethylsilyl)-3-ethyl-4-oxoazetidine-2-carboxylic acid (Tetrahedron, 46(7), 2255-62; 1990, 100 mg, 0.388 mmol) was dissolved in N,N-dimethylformamide (2 mL) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (418 mg, 1.10 mmol) was added. The reaction mixture was stirred for 20 minutes then 4-(tert-butyl)benzene-1,2-diamine (165 mg, 1.00 mmol) was added and the reaction mixture stirred at ambient temperature for 18 hours. The reaction mixture was diluted with water and extracted three times with ethyl ether. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent removed in-vacuo. The residue was purified by silica gel column chromatography eluting with 0-100% ethyl acetate in hexanes to afford the amide as a mixture of isomers.

Provenance & Evidence