tert-butyl N-(2,3-dihydroxypropyl)carbamate → tert-butyl N-(2-oxoethyl)carbamate

Participants

Reaction Steps

3-(Boc-amino)-1,2-propanediol (21g, 110 mmol) was dissolved in water (200 ml) and stirred with potassium m-periodate (25.3g, 110 mmol) at room temperature under argon for 2h. The reaction mixture was filtered and washed with methylene chloride (100 ml). The aqueous layer was extracted with methylene chloride (3×150 ml). The organic extract was washed with brine (SOmI), dried and evaporated to dryness to give a light pink oil. This oil was purified by flash column chromatography using silica gel and CH2Cl2/ethyl acetate as the eluent. Yield was 14g (80%). 1HNMR (CDCl3) d 1.45 (s, 9H, t-Butyl), 4.08 (d, 2H, CH2), 5.24 (bs, 1H, NH) and 9.67 (s, 1H, CHO).

Provenance & Evidence