[CH:1]([C:3]1[S:4][C:5]([CH:13]([CH3:15])[CH3:14])=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1)=O.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:14][CH:13]([C:5]1[S:4][C:3]([CH2:1][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[N:7][C:6]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:15]Ethyl 2-formyl-5-(1-methylethyl)-1,3-thiazole-4-carboxylate (150 mg) was dissolved in anhydrous DCM (10 ml) and morpholine (0.064 ml) was added and the mixture stirred under nitrogen for 2 h at RT. Sodium triacetoxyborohydride (280 mg) was added and the mixture stirred at RT for 18 h. Sodium bicarbonate (20 ml) and DCM (20 ml) were added and separated by hydrophobic frit. The solvent was removed in vacuo and purified by column chromatography on silica gel (10 g silica), eluting with a gradient of 0-100% ethyl acetate in cyclohexane to give the title compound as a yellow oil (77 mg).
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