Hydrochloric Acid → (3aR,6aR)-5-Methyloctahydropyrrolo[3,4-b]pyrrole
Reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]2[CH2:13][N:14]([CH3:16])[CH2:15][C@H:9]12)=O)(C)(C)C.Cl>CO>[CH3:16][N:14]1[CH2:13][C@@H:10]2[C@@H:9]([NH:8][CH2:12][CH2:11]2)[CH2:15]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the product of Example A6 (20.8 g, 0.86 mole) in MeOH (450 ml) was added aqueous 3N HCl (300 ml). The mixture was stirred at room temperature overnight, then concentrated to dryness at 30° C. under vacuum. The residue was treated with aqueous 1N NaOH to obtain a pH of 9-10. The mixture was concentrated to dryness. The crude material was purified by chromatography (eluting with a mixture of 10% MeOH and 1% NH4OH in dichloromethane) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 4.12-4.17 (m, 1 H) 3.31-3.43 (m, 1 H) 3.19-3.30 (m, 1 H) 3.12 (d, J=11.53 Hz, 1 H) 2.88-3.01 (m, 1 H) 2.69 (dd, J=9.49, 2.37 Hz, 1 H) 2.40-2.52 (m, 2 H) 2.33 (s, 3 H) 2.12-2.28 (m, 1 H) 1.82-1.95 (m, 1 H). MS: (M+H)+=127.