Diisopropylethylamine → 1,1-Dimethylethyl 2-[[(methylsulfonyl)oxy]methyl]-2-(hydroxymethyl)-4-morpholinecarboxylate

Participants

Reaction Steps

To a solution of (2S) 1,1-dimethylethyl 2-(hydroxymethyl)-4-morpholinecarboxylate (5.63 g) (Heterocycles, 1993, 35, 105) and N-ethyl-N,N-diisopropylamine (9 ml) in dichloromethane (200 ml) at room temperature was added methanesulfonic anhydride (5.42 g). The reaction was stirred for 16 hours. The reaction mixture was poured onto saturated aqueous NaHCO3 solution and the organics were extracted with dichloromethane. The combined organic extracts were dried with MgSO4 and concentrated to give an oil (8.33 g). This was used without further purification.

Provenance & Evidence