Trifluoroacetic acid → HCID 86602087, compound

Participants

Reaction Steps

Pinane acetonide butylamide 8 (107 mg, 0.35 mmol) was stirred with a 1:1 mixture of trifluoroacetic acid (TFA)/water (3 ml) at room temperature. The reaction was monitored by TLC and showed about 75% conversion to the cis-diol after 2 hours, then the reaction stalled and the intensity of a new spot between starting material and product started to build up. The unknown byproduct may be formed from fragmentation of the pinane ring in product 9 under the acidic condition. The optimal reaction time was about 3.5 hours. The reaction mixture was neutralized with saturated NaHCO3 solution, and then was extracted 3 times with 50% EtOAc/hex. The combined organic extract was washed with H2O, dried over anhydrous Na2SO4 and concentrated. Residual unreacted starting material 8 and byproduct from the pinanediol butylamide 9 was not removed by silica chromatography. IR (CHCl3): 3455, 3390, 3000, 2960, 2930, 2875, 1647, 1530, 1463, 1385, 1140, 1117, 1054, 1033 and 1018 cm−1.

Provenance & Evidence