4-Nitrobenzoic Acid → HCID 25133552, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (S)-8a (46 mg, 0.35 mmol), p-nitrobenzoic acid (86 mg, 0.52 mmol), and triphenylphosphine (181 mg, 0.69 mmol), diisopropylazodicarboxylate (135 μL, 0.69 mmol) was added dropwise and the resulting mixture was stirred at 23° C. overnight. The solvent was removed under reduced pressure and the residue was purified by flash-chromatography (1:3 EtOAc/Hex). The resulting ester was dissolved in a 3:2:1 mixture of THF, methanol and water (4 mL) and LiOH.H2O (72 mg, 1.7 mmol) was added. The yellow mixture was stirred at 23° C. overnight and then the solvent was removed in vacuo, the residue was diluted with water and the aqueous phase was extracted with ether. The organic extracts were dried (Na2SO4) and the solvent evaporated. Purification of the residue by flash-chromatography (EtOAc) afforded 20 mg (44%) of (R)-8c as a colourless liquid. [α]D20=+12.1 (c 1.4, CHCl3). 1H and 13C NMR are consistent with those reported for the (S)-enantiomer 8a

Provenance & Evidence