Sodium triacetoxyborohydride → HCID 70832977、化合物

反応式

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([CH:14]3[CH2:18][CH2:17][CH2:16][NH:15]3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[N:19]1([C:24]2[N:29]=[C:28]([C:30](=O)[CH3:31])[CH:27]=[C:26]([CH3:33])[N:25]=2)[CH:23]=[CH:22][N:21]=[CH:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12]([CH:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH:30]([C:28]3[CH:27]=[C:26]([CH3:33])[N:25]=[C:24]([N:19]4[CH:23]=[CH:22][N:21]=[CH:20]4)[N:29]=3)[CH3:31])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

参加物

実験手順

Pyrrolidine-2-carboxylic acid (benzo[1,3]dioxol-5-ylmethyl)-amide (85 mg, 0.34 mmol) was dissolved in dioxane (2.5 mL). Next, TsOH monohydrate (30 mg) and the 1-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-ethanone (69 mg, 0.34 mmol) were added and the reaction mixture was microwaved for 20 mins at 130° C. Upon completion of heating, the solution was allowed to return to room temperature and the sodium triacetoxyborohydride (145 mg, 0.68 mmol) was added to the reaction vessel and it was allowed to stir at room temperature for an additional 16 hours. After this period, the solution was concentrated under vacuum, diluted in ethyl acetate (50 mL) and transferred to a separatory funnel. The organic layer was washed with 1M NaOH (50 mL), dried over Na2SO4 and concentrated down by vacuum to afford the crude product. This material was purified by Flash Chromatography (0-40% ACN/DCM gradient) to afford 12 mg (8%) of 1-[1-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-ethyl]-pyrrolidine-2-carboxylic acid (benzo[1,3]dioxol-5-ylmethyl)-amide. Product isolated as a mixture of diasteromers; [M+H]+ 435.03.