Triethylamine → HCID 56941483, compound

Participants

Reaction Steps

Cyclopropylacetic acid (0.019 mL, 0.25 mmol) was added portionwise to a stirred solution of 4,5,6,7-tetrahydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine (0.047 g, 0.21 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.078 g, 0.21 mmol), and triethylamine (0.043 mL, 0.31 mmol) in a mixture of THF (0.5 mL) and DMF (0.5 mL). The reaction mixture was stirred at room temperature for 15 hours and diluted with a saturated solution of NaHCO3. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield 5-(cyclopropylacetyl)-4,5,6,7-tetrahydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine (0.043 g, 67% yield) as an oil. C18H20N2O3. (mixture of rotamers 70:30) 1H NMR (400 MHz, CDCl3) δ ppm 0.10-0.27 (m, 2 H), 0.50-0.66 (m, 2 H), 0.98-1.16 (m, 1 H), 2.33 (d, J=6.7 Hz, 0.6 H), 2.38 (d, J=6.7 Hz, 1.4 H), 2.59-2.82 (m, 2 H), 3.72 (t, J=5.7 Hz, 1.4 H), 3.92 (t, J=5.7 Hz, 0.6 H), 4.52 (br. s, 0.6 H), 4.71 (br. s, 1.4 H), 5.11 (s, 1.4 H), 5.12 (s, 0.6 H), 6.81-7.01 (m, 1 H), 7.02 (d, J=7.9 Hz, 2 H), 7.27-7.46 (m, 2 H).

Provenance & Evidence