Sodium Hydroxide → HCID 53338743, compound

Participants

Reaction Steps

A solution of the protected methylether 23 (0.320 g, 1.29 mmol) in THF (3 mL) and 4 M H2SO4 (9 mL) was heated at 55° C. for 5 h. After cooling, the reaction contents were poured into 20 mL of cold (−10° C.) 4 M NaOH and diluted with 20 mL of saturated NaHCO3. The mixture was extracted with CH2Cl2 (4×15 mL) and the combined extracts dried (K2CO3) and concentrated to provide 24 as a pale oily solid (0.274 g, 96% yield). This product was of adequate purity for the subsequent transformations. 1H NMR (400 MHz, CDCl3): δ 1.85 (t, J=10.3 Hz, 1H), 2.11 (td, J=3.3, 11.0 Hz, 1H), 2.35 (bs, 1H, NH), 2.74 (m, 2H, triplet shape), 2.90 (m, 1H, td shape), 2.96-3.06 (m, 2H), 3.25-3.36 (m, 5H, OCH3 singlet present at 3.33), 3.50 (m, AB pattern, J=13.2 Hz, 2H), 7.22-7.33 (m, 5H); 13C NMR (100 MHz, CDCl3): δ 45.2, 53.8, 54.4, 55.9, 59.0, 63.4, 75.1, 126.9, 128.1, 129.1, 138.0. HRMS Calcd. for [C13H20N2O+H+] 221.1654. Found 221.1654. [α]D25+14.4 (c 0.030, CHCl3).

Provenance & Evidence