(3aR,6aR)-5-methyl-1-(4'-(1-trityl-1H-pyrazol-4-yl)biphenyl-4-yl)octahydropyrrolo[3,4-b]pyrrole → (3aR,6aR)-1-(4'-(1H-pyrazol-4-yl)biphenyl-4-yl)-5-methyloctahydropyrrolo[3,4-b]pyrrole
Reaction equation
[CH3:1][N:2]1[CH2:9][C@@H:8]2[C@@H:4]([N:5]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]5[CH:23]=[N:24][N:25](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[CH:26]=5)=[CH:18][CH:17]=4)=[CH:12][CH:11]=3)[CH2:6][CH2:7]2)[CH2:3]1>C(O)=O>[NH:24]1[CH:23]=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:13]3[CH:12]=[CH:11][C:10]([N:5]4[CH2:6][CH2:7][C@@H:8]5[CH2:9][N:2]([CH3:1])[CH2:3][C@H:4]45)=[CH:15][CH:14]=3)=[CH:17][CH:18]=2)[CH:26]=[N:25]1Participants
3
Procedure
The product of Example 81A (44 mg, 0.075 mmole) was stirred with 3 ml of formic acid for 4 hours. The mixture was concentrated to dryness and the residue was dissolved in 10% methanol in dichloromethane and stirred with saturated sodium bicarbonate. Two layers were separated and the aqueous layer was extracted with dichloromethane (2×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.88 (s, 2H) 7.47-7.64 (m, 6H) 6.65 (d, J=8.81 Hz, 2H) 4.11-4.25 (m, 1H) 3.50-3.66 (m, 1H) 3.25-3.37 (m, 1H) 2.92-3.07 (m, 1H) 2.71-2.82 (m, 1H) 2.51-2.69 (m, 3H) 2.34 (s, 3H) 2.13-2.25 (m, 1H) 1.90-2.05 (m, 1H). MS: (M+H)+=345.