Sodium Bicarbonate → HCID 67337045, compound

Reaction equation

[CH2:1]([O:3][C@H:4]([CH3:41])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:18][NH:17][CH2:16][C@H:15]2[CH2:37][NH:38][CH:39]=O)=[CH:10][CH:9]=1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:3][C@H:4]([CH3:41])[CH2:5][O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C@@H:14]2[C@@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:18][NH:17][CH2:16][C@H:15]2[CH2:37][NH:38][CH3:39])=[CH:12][CH:13]=1)[CH3:2]

Participants

Procedure

A solution of 1 mmol of N-{(3S,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidin-3-ylmethyl}-formamide (example 7) 8 ml of THF is mixed with 2 mmol of LiAlH4 (1M in THF) and stirred at RT for 13 h (conversion checked by HPLC or TLC), then the reaction mixture is heated to 40° C. for 2 h. The reaction mixture is poured on saturated aqueous NaHCO3 solution and extracted with TBME (3×). The combined organic phases are washed with H2O and brine and evaporated in vacuo. The title compound is obtained from the residue by flash chromatography (SiO2 60F) and identified based on the Rf value.