Acetic Acid → HCID 86628317, compound

Participants

Reaction Steps

In a similar manner to Step 2 of Example 6, 4-(2-cyanobenzenesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (0.140 g, 0.238 mmol) was dissolved in acetonitrile (6.0 mL), and the solution was treated with pyrrolidine (0.398 mL, 4.77 mmol), acetic acid (0.273 mL, 4.77 mmol) and sodium triacetoxyborohydride (0.151 g, 0.715 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=85/15, 80/20) to obtain 4-(2-cyanobenzenesulfonyloxy)-5-methoxy-7-[1-(tert-butoxycarbonyl)-5-(pyrrolidin-1-ylmethyl)indol-2-yl]isoindolinone (0.0773 g, ESI-MS m/z: 643 [M+H]+; 1H-NMR (CD3OD)8(ppm): 1.18 (s, 9H), 1.83-1.92 (m, 4H), 2.88-2.96 (m, 4H), 3.25 (s, 3H), 4.04 (s, 2H), 4.49 (s, 2H), 6.55 (s, 1H), 7.00 (s, 1H), 7.28 (dd, J=1.6, 8.7 Hz, 1H), 7.52 (d, J=1.6 Hz, 1H), 7.77-7.93 (m, 3H), 8.08 (dd, J=1.6, 7.3 Hz, 1H), 8.17 (d, J=8.7 Hz, 1H).

Provenance & Evidence