Oxalic Acid → HCID 69734306, compound

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]([CH3:24])=[C:13]3[C:21](=O)[NH:20][CH2:19][C@@H:18]([CH3:23])[N:14]3[C:15]=2[C:16]=1[CH3:17].[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27]>C(O)C>[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]([CH3:24])=[C:13]3[CH2:21][NH:20][CH2:19][C@@H:18]([CH3:23])[N:14]3[C:15]=2[C:16]=1[CH3:17]

Participants

Procedure

Lithium aluminium hydride (64 mg, 1.67 mmol) was added in portions to a solution of (R)-7-chloro-4,6,10-trimethyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (200 mg, 0.76 mmol) and the resulting suspension was heated to reflux for 5 h. After cooling the reaction was quenched by careful addition of 1 M aqueous sodium potassium tartrate solution (20 mL). Then ether (20 mL) was added; the organic layer was separated, washed with brine, dried (Na2SO4), and evaporated. The residue was dissolved in ether (3 mL) and treated with a solution of oxalic acid (200 mg, 2.22 mmol) in ethanol (1 mL). The precipitate was collected by filtration and dried to yield the title compound (116 mg, 45%). Off-white solid. ISP-MS: m/e=249.2 ([M+H−C2H2O4]+). Anal. calc. for C16H19ClN2O4 (338.79): C 56.72; H 5.65; N 8.27; found: C 56.64; H 5.41; N 8.22.