Acetone → HCID 68760434, compound

Participants

Reaction Steps

A stirring solution of (1′-benzyl-1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methanamine (0.250 g, 0.43 mmol) in DCE (3 mL) was treated with acetone (0.159 mL, 2.17 mmol). The reaction was allowed to stir for 20 minutes, followed by the addition of NaBH(OAc)3 (0.184 g, 0.87 mmol). The reaction was stirred at room temperature overnight. An additional 2.5 equivalents of acetone and 1.0 equivalent of NaBH(OAc)3 were added to the reaction and stirred an additional 2 hours. The reaction was quenched by the addition of saturated NaHCO3 and diluted with DCM. The combined organics were washed with brine, dried Na2SO4, filtered, and concentrated under reduced pressure to give N-((1′-benzyl-1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)propan-2-amine (0.185 g, 84%), which was used without further purification. LCMS (APCI+) m/z 536.4 [M+H]+; Rt=3.61 min.

Provenance & Evidence