[C:1]([NH:8][C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl.C(OCC)C>[C:1]([NH:8][C:9]([CH3:13])([CH3:12])[CH:10]=[O:11])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]
The resulting N-BOC-2-amino-2-methyl-1-propanol (3.69 g, 19.5 mmol) was dissolved in methylene chloride (74 ml) and added to a stirred suspension of Dess-Martin periodinane (10.75 g, 25.35 mmol; Aldrich Chemical Company, Milwaukee, Wis.) in methylene chloride (89 ml). After stirring for 20 minutes under nitrogen, the reaction mixture was diluted with diethyl ether (370 ml), poured into sodium hydroxide (148 ml, 1.3M) and stirred for ten minutes. The aqueous sodium hydroxide layer was separated and discarded. The remaining organic solution was washed successively with sodium hydroxide (148 ml, 1.3M) and H2O (185 ml). After drying over magnesium sulfate, the solvent was removed in vacuo to yield 3.21 grams of N-BOC-2-amino-2-methyl-1-propanal.
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