Aminoacetaldehyde dimethyl acetal → HCID 24991638, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-benzyl-1-(3-fluorophenyl)-1,8-diazaspiro[4.5]decane-2,4-dione (Intermediate 1A.4-1, 100 mg, 0.29 mmol) in methanol (0.1 ml) was added 2,2-dimethoxyethylamine (2 ml). The reaction was allowed to stir at 100° C. until the starting material was consumed. The reaction was concentrated in vacuo, and the residue was dissolved in toluene. The reaction was treated with a catalytic amount of p-toluenesulfonic acid and allowed to stir at 110° C. for 18 h. The crude reaction was purified via reverse phase chromatography to yield 1-benzyl-5′-(3-fluorophenyl)-1′H-spiro[piperidine-4,6′-pyrrolo[3,4-b]pyrrol]-4′(5′H)-one. LCMS (M+H) 376.1. 1H NMR (400 MHz, CD3OD) δ 7.50 (m, 7H), 7.23 (td, J=8.4, 2.1 Hz, 2H), 7.07 (m, 3H), 6.43 (d, J=2.8 Hz, 1H), 4.41 (s, 2H), 3.64 (d, J=13.6 Hz, 2H), 3.43 (t, J=12.6 Hz, 3H), 2.28 (td, J=14.1, 4.0 Hz, 2H), 2.02 (d, J=15.6 Hz, 2H).

Provenance & Evidence