Triacetoxyperiodinane → [1-(Benzooxazole-2-carbonyl)-propyl]-carbamic acid tert-butyl ester
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28](=[O:44])[NH:29][CH:30]([CH:33]([C:35]1[O:36][C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[N:39]=1)[OH:34])[CH2:31][CH3:32])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([O:27][C:28](=[O:44])[NH:29][CH:30]([C:33]([C:35]1[O:36][C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[N:39]=1)=[O:34])[CH2:31][CH3:32])([CH3:24])([CH3:25])[CH3:26]Participants
4
Procedure
Dess-Martin Periodinane (15 wt % in DCM, 8.8 g, 3.1 mmol) was added to a solution of [1-(Benzooxazol-2-yl-hydroxy-methyl)-propyl]-carbamic acid tert-butyl ester (475 mg, 1.55 mmol) in dry methylene chloride (15 ml) and stirred at room temperature for 4 hrs. The reaction was quenched with a solution of Na2S2O3 in aqueous NaHCO3. The organic layer was separated and the aqueous extracted with dichloromethane. The organic extracts were dried over sodium sulfate and concentrated under reduced pressure. Column chromatography on silica eluting with a mixture of heptane and methylene chloride gave the title compound as a off-white powder (0.38 g).