Boron Trichloride → HCID 89783326, compound

Participants

Reaction Conditions

Reaction Steps

To a 100-mL round-bottomed flask was added (6R)-6-((benzyloxy)methyl)-2-(3-(tert-butylamino)-2-methyl-5-quinoxalinyl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one and (6S)-6-((benzyloxy)methyl)-2-(3-(tert-butylamino)-2-methyl-5-quinoxalinyl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (468) (0.55 g, 1.20 mmol) and DCM (15 mL). The reaction mixture was cooled to 0° C. and under a nitrogen atmosphere boron trichloride (2.40 mL, 2.40 mmol, 1 M in DCM) (Sigma-Aldrich) was added dropwise. The reaction mixture was stirred at 0° C. for 30 min and at RT for 1 h. The reaction was quenched by the addition of NaHCO3 (200 mg in MeOH, 5 mL) and the solvent was removed under vacuum. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 4% 2M NH3/MeOH in DCM to provide 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6-(hydroxymethyl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (469) (0.25 g, 57% yield, 50% ee) as a yellow solid and as a mixture of enantiomers. 1H NMR (400 MHz, DMSO-d6) δ 11.91 (s, 1H), 7.86 (dd, J=1.37, 7.63 Hz, 1H), 7.63 (dd, J=1.37, 8.02 Hz, 1H), 7.58 (s, 1H), 7.36 (t, J=7.73 Hz, 1H), 6.88 (d, J=1.57 Hz, 1H), 6.02 (s, 1H), 5.09 (t, J=5.58 Hz, 1H), 4.48 (t, J=6.06 Hz, 1H), 3.66 (td, J=5.53, 10.86 Hz, 1H), 3.54 (td, J=6.16, 10.76 Hz, 1H), 2.56 (br. s., 3H), 1.56 (s, 9H). m/z (ESI, +ve) 366.0 (M+H)+.

Provenance & Evidence