Sodium Bicarbonate → HCID 25133550, compound

Participants

Reaction Conditions

Reaction Steps

Compound 7a (0.27 g, 0.74 mmol) was dissolved in dry THF (5 mL) and TBAF (1.0 M solution in THF, 0.81 mL, 0.81 mmol) was added. The resulting mixture was stirred at 23° C. overnight, afterward a saturated solution of NaHCO3 was added, the solvent was removed and the aqueous phase was extracted with EtOAc. The organic extracts were dried and evaporated and the residue was purified by flash-chromatography (EtOAc) to afford 76 mg (77%) of 8a as a colourless oil: [α]D20, −12.6 (c 1.6, CHCl3); 1H NMR (CDCl3) δ 4.65 (d, J=6.0 Hz, 1H), 4.57 (d, J=6.0 Hz, 1H), 4.92-3.81 (m, 2H), 3.75-3.60 (m, 2H), 3.55 (dd, J=3.4, 12.1 Hz, 1H), 2.96 (bs, 1H), 1.95-1.69 (m, 3H), 1.65-1.53 (m, 1H); 13C NMR (CDCl3) δ 94.9, 73.7, 69.3, 68.2, 30.2, 24.7.

Provenance & Evidence