Acetic Acid → HCID 86757713, compound

Participants

Reaction Steps

(4aR, 12aR)-4a-(3-benzyloxyphenyl)-1,2,3,4,4a,5,12,12a-octahydroquinolino[2, 3-g]isoquinoline (84 mg), and cyclopropanecarboaldehyde (0.0305 ml, 0.40 mmol) were dissolved in dry THF (4 ml), and triacetoxysodium borohydride (84. 8 mg, 0.40 mmol) and acetic acid (0.0126 ml, 0.22 mmol) were added to the resultant solution, followed by stirring at room temperature for 2 hours. A saturated aqueous sodium bicarbonate solution (30 ml) and water (30 ml) were then added to the solution, and the resultant mixture was extracted with chloroform (100 ml, twice). The organic layers were dried over sodium sulfate, and then concentrated. The residue was purified by using a silica gel column to obtain (4aR, 12aR)-2-cyclopropylmethyl-4a-(3-benzyloxyphenyl)-1,2,3,4,4a,5,12,12a-octahydroquinolino[2, 3-g]isoquinoline (78 mg, 82% in two steps).

Provenance & Evidence