Ammonium Acetate → HCID 67975592, compound

Reaction equation

C([O-])(=O)C.[NH4+].C[O:7][C:8](=O)[CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=O.C([BH3-])#[N:22].[Na+]>CO>[NH:22]1[C:8](=[O:7])[CH2:9][CH:10]2[CH2:18][C:17]3[C:12]([CH:11]12)=[CH:13][CH:14]=[CH:15][CH:16]=3

Participants

Procedure

A solution of ammonium acetate (3.77 g, 48.9 mmol) was coevaporated in anhydrous methanol. Then, (1-Oxo-indan-2-yl)-acetic acid methyl ester H1 (1.00 g, 4.89 mmol) in methanol (40 mL) was added followed by molecular sieves (4.9 g). The solution was stirred for 30 min and sodium cyanoborohydride (0.92 g, 14.9 mmol) was added. The suspension was refluxed for 40 h. The solution was filtered through celite. A saturated solution of sodium hydrogenocarbonate was added and the solution was extracted with ethyl acetate (3*50 mL). The combined organic layers were washed with hydrogen chloride (1N), brine, dried and concentrated. The residue was purified by flash chromatography eluting with ethyl acetate and then ethyl acetate/methanol (95/5) to give 3,3a,4,8b-tetrahydro-1H-indeno[1,2-b]pyrrol-2-one G1 (White solid, 300 mg, 35%). LCMS (method A) RT 1.17; ES 196, 174; IR 3233, 1689 cm−1; Mp: 150-153° C.; 1H NMR (400 MHz, CD3OD) δ 7.34 (1H, d), 7.12-7.27 (3H, m), 5.04 (1H, d), 3.22-3.37 (2H, m), 2.83 (1H, d), 2.70 (1H, dd), 2.15 (1H, dd) ppm.