Sodium Thiosulfate → tert-Butyl N-(3-oxopropyl)carbamate

Participants

Reaction Steps

To a solution of tert-butyl N-(3-hydroxypropyl)carbamate (0.177 g, 1.01 mmol) in CH2Cl2 (5 mL) was added Dess-Martin periodinane (0.545 g, 1.28 mmol) and the resultant mixture was stirred at room temperature for 2.5 hours. The mixture was diluted with ether (20 mL) and treated with 20% aqueous Na2S2O3 (5 mL) and saturated aqueous NaHCO3 (5 mL). After 10 minutes the mixture became clear and colorless and the phases were separated. The aqueous phase was extracted with ether (3×10 mL). The combined organic extracts were washed sequentially with 20% aqueous Na2S2O3 (10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL), dried (MgSO4), and concentrated to provide 0.127 g (96%) of N-(tert-butoxycarbonyl)-3-amino-propionaldehyde as a colorless oil. 1H NMR (CDCl3) δ 1.43 (s, 9H), 2.71 (t, 2H, J=6.0 Hz), 3.42 (m, 2H), 4.89 (br s, 1H), 9.81 (s, 1H).

Provenance & Evidence