Trifluoroacetic acid → HCID 59464032, compound

Participants

Reaction Steps

To an ice water cooled solution of benzyl [6-(1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]carbamate, prepared as above, (4.94 g, 13.41 mmol) was added TFA (20 mL) followed by water (1.1 mL). The reaction mixture was allowed to stir at ambient temperature for 2 hours. It was treated with 2M NaOH to adjust the pH to 10 and then the mixture was extracted into EtOAc (3×200 mL), the organic phase was separated, dried (MgSO4) and concentrated to leave a gum, 4.05 g (12.26 mmol, 93%) which was used directly in the next stage; 1H NMR (CDCl3) δ 1.97-2.10 (m, 2H), 2.24-2.29 (m, 2H), 2.49-2.53 (m, 4H), 3.13-3.21 (m, 1H), 5.22 (s, 2H), 6.82 (s, 1H), 7.18 (d, 1H), 7.36-7.40 (m, 5H), 7.96 (s, 1H), 8.41 (s, 1H); MS m/e MH+ 325.

Provenance & Evidence