Methanesulfonyl chloride → (R)-N-(methylsulfonyloxy)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride

Participants

Reaction Steps

To a solution of (R)-N-hydroxy-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride (10.4 g, 47.3 mmol) cooled to 0° C. in THF (150 mL) was added methanesulfonyl chloride (5.97 g, 52.1 mmol) followed by N-ethyl-N-isopropylpropan-2-amine (6.75 g, 52.1 mmol) and the reaction stirred for 1 hr at ambient temperature. The reaction was concentrated in vacuo. The material was dissolved in dichloromethane and chromatographed using 8:1 Hexane/EtOAc to 4:1 Hexane/EtOAc (2 columns) to give the (R)-N-(methylsulfonyloxy)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride as a viscous oil that solidified on standing (12 g, 40 mmol, 85% yield).

Provenance & Evidence