Hydrogen chloride-ethyl acetate → HCID 86702796, compound

Participants

Reaction Steps

(1R,4S)-7-tert-butyl 2,3-dimethyl 7-azabicyclo[2.2.1]heptane-2,3,7-tricarboxylate (XLVIII) (3.28 g, 10.49 mmol) was dissolved in EtOAc (20 mL) and treated with 1M HCl/EtOAc (20 mL) and stirred for 15 minutes at room temperature. The solvent was removed under vacuum and the oily residue triturated with Et2O to give (1R,4S)-dimethyl 7-azabicyclo[2.2.1]heptane-2,3-dicarboxylate (LXIX) as a light pink solid (2.46 g, 9.86 mmol, 94% yield). 1H NMR (DMSO-d6) (two isomers in a 4/1 ratio) δ ppm [1.41-1.53 (m, 2nd isomer), 1.77-1.83 (m, 1st isomer), 2H], [1.63-1.72 (m, 2nd isomer), 1.93-2.02 (m, 1st isomer), 2H], [3.16 (d. J=6 Hz, 2nd isomer), 3.38 (brs, 1st isomer), 2H], [3.57 (s, 1st isomer), 3.62 (s, 2nd isomer), 6H], [4.34 (brs, 1st isomer), 4.40 (d, J=4 Hz, 2nd isomer), 2H], [9.68 (brs, 1st isomer), 9.92 (brs, 2nd isomer, 2H]. ESIMS found for C10H15NO4 m/z 214 (M+H).

Provenance & Evidence