[OH-:1].[Na+].[C:3]([O:7][C:8]([NH:10][CH:11]1[CH2:13][CH:12]1[CH:14]=[CH2:15])=[O:9])([CH3:6])([CH3:5])[CH3:4].C1COCC1.[Mn]([O-])(=O)(=O)=O.[K+].[OH2:27]>>[C:3]([O:7][C:8]([NH:10][CH:11]1[CH2:13][CH:12]1[CH:14]([OH:27])[CH2:15][OH:1])=[O:9])([CH3:6])([CH3:5])[CH3:4]Sodium hydroxide solution (114 mg in 10 mL of water) was added to N-tert-butoxycarbonyl-2-ethenylcyclopropylamine (59 mg, 0.3 mmol), from Step C of Example 1, until the N-tert-butoxycarbonyl-2-ethenylcyclopropylamine oiled out to form a separate organic layer. THF (10 mL) was added until a cloudy solution was formed. An additional 2.5 mL of water was added and the solution became clear. The clear colorless solution was cooled to 0° C. in an ice-water bath. A solution of potassium permanganate (80 mg, 0.5 mmol) in 10 mL of water was added and the cold reaction mixture was stirred vigorously for 5 minutes at 5° C. TLC analysis (on silica gel plates eluted with 25% ethyl acetate in hexane) showed that all of the starting material had been consumed in the reaction. The reaction mixture was concentrated in vacuo and the residue dissolved in water. The resultant aqueous solution was extracted 3 times with ethyl acetate. The combined ethyl acetate layers were dried over anhydrous sodium sulfate and concentrated in vacuo. N-tert-Butoxycarbonyl-2-(1',2'-dihydroxyethyl)cyclopropyl amine was obtained in 86% crude yield (56 mg) as a clear colorless oil. The crude product was carried on to Step B without further purification. DCI NH3MS, M/Z: 218 (M+H)+, 235 (M+NH4)+.
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