Red-Al → 4-(3,3,7-Trimethylindolin-6-yl)morpholine

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Reaction Steps

To a solution of 3,3,7-trimethyl-6-morpholinoindolin-2-one (45.7 mg, 0.176 mmol) in toluene (10 mL) at 80° C. under N2, Red-Al (0.18 mL, 3M, 0.53 mmol) was added dropwise. The resultant mixture was stirred at 80° C. for 2 h. The mixture was cooled to rt and quenched with NaOH (2 mL, 3N). The mixture was diluted with EtOAc and washed with water and brine, dried and concentrated. Purification of the residue by flash chromatography over silica gel, using 40% EtOAc in hexane, gave 4-(3,3,7-trimethylindolin-6-yl)morpholine (33.1 mg, 76%): 1H-NMR (DMSO-d6) δ 6.74 (1H, d, J=8.0 Hz), 6.29 (1H, d, J=8.0 Hz), 5.11 (1H, s), 3.69 (4H, s), 3.16 (2H, s), 2.72 (4H, s), 1.96 (3H, s), 1.18 (6H, s). Mass Spectrum (ESI) m/e=247.1 (M+1).

Provenance & Evidence