(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxypropanoic acid → 6-(methoxymethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one

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Reaction Steps

6-(Methoxymethyl)-5,6-dihydropyrrolo[3,4-b]pyrrolo-4(1H)-one (485a) was prepared in a manner similar to that described for Intermediate 702, starting from (R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropanoic acid (prepared according to the procedure in WO 2012/051551). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.32 (br. s., 1H), 7.58 (s, 1H), 6.83 (d, J=2.74 Hz, 1H), 6.09 (d, J=2.74 Hz, 1H), 4.50 (ddd, J=6.75, 5.58, 1.37 Hz, 1H), 3.37-3.49 (m, 2H), 3.30 (s, 3H). m/z (ES, +ve) 167.0 (M+H)+. 6-(Methoxymethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (485b) was prepared in a manner similar to that described for Intermediate 705, using 6-(methoxymethyl)-5,6-dihydropyrrolo[3,4-b]pyrrolo-4(1H)-one (485a) as the starting material. 1H NMR (400 MHz, CDCl3) δ ppm 6.93 (d, J=1.76 Hz, 1H), 5.85 (s, 1H), 4.56-4.65 (m, 1H), 3.55 (dd, J=8.61, 7.04 Hz, 1H), 3.40-3.47 (m, 4H), 1.30-1.36 (m, 12H). m/z (ES, +ve) 293.1 (M+H)+.

Provenance & Evidence