Sodium Hydroxide → HCID 59849173, compound

Participants

Reaction Steps

To a solution of 2-methyl-7-nitro-4-(4-oxo-piperidin-1-yl)-2,3-dihydro-isoindol-1-one (4.2 g, 14.5 mmol) and piperazine-1-carboxylic acid tert-butyl ester (3.24 g, 17.4 mmol) in 1,2-dichloroethane is added sodium triacetoxy borohydride (3.69 g, 17.4 mmol) at 0° C. under nitrogen atmosphere. After the mixture is stirred at room temperature for 5 hours, 1N sodium hydroxide aqueous solution is added at 0° C. The mixture is extracted with dichloromethane and the organic layer is washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography (AcOEt; AcOEt: MeOH=9: 1) to give 4-[1-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)-piperidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (4.16 g, 62%). 1H-NMR (400 MHz, CDCl3, δ, ppm): 1.47 (s, 9H), 1.66-1.76 (m, 2H), 1.94-2.02 (m, 2H), 2.42-2.59 (m, 5H), 2.84-2.93 (m, 2H), 3.05 (s, 3H), 3.40-3.49 (m, 4H), 3.49-3.57 (m, 2H), 4.35 (s, 2H), 7.00 (d, 1H), 7.76 (d, 1H).

Provenance & Evidence