HCID 11109638, compound → HCID 86702795, compound

Participants

Reaction Steps

(1R,4S)-7-tert-butyl 2,3-dimethyl 7-azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylate (XLVII) (3.41 g, 11.04 mmol) was dissolved in MeOH (50 mL) under an argon atmosphere. Adams' catalyst was added and the reaction was flushed with hydrogen. The mixture was stirred under hydrogen overnight at room temperature. The catalyst was filtered off and the solvent was removed in vacuo to give a yellow oil. The oily residue was crystallized from hot heptane to give (1R,4S)-7-tert-butyl 2,3-dimethyl 7-azabicyclo[2.2.1]heptane-2,3,7-tricarboxylate (XLVIII) as a white solid (3.28 g, 10.49 mmol, 95% yield). 1H NMR (CDCl3) (two isomers in a 3/1 ratio) δ ppm [1.40 (s, 2nd isomer), 1.44 (s, 2nd isomer), 9H], 1.60-2.00 (m, 4H), [3.66 (s, 1st isomer), 3.71 (s, 2nd isomer), 6H], [4.37 (brs, 1st isomer), 4.51 (brs, 2nd isomer), 2H]; ESIMS found for C15H23NO6 m/z 336 (M+Na).

Provenance & Evidence