Methanesulfonyl chloride → HCID 86636652, compound

Participants

Reaction Steps

To a solution of (3S)-1-Boc-3-[(4,4-dimethylcyclohexyl)(3-hydroxy-2,2-dimethylpropanoyl)amino]pyrrolidine (300 mg, 0.76 mmol) prepared in Step B of Example A8 in DCM was added TEA (192 mg, 1.9 mmol), slowly added dropwise methanesulfonylchloride (104 mg, 0.91 mmol) at 0° C., and the solution was heated to rt, and stirred for 1 h. After the reaction finished, the solvent was concentrated in vacuo, and washed with water and EtOAc. The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (eluent: EtOAc/Hex=1/2) to give (3S)-1-Boc-3-[(4,4-dimethylcyclohexyl){2,2-dimethyl-3-[(methylsulfonyl)oxy]propanoyl}amino]pyrrolidine (250 mg, 75%). A solution of this compound (200 mg, 0.42 mmol) in THF was added dropwise TBAF (in THF, 1.0M 0.5 ml, 0.5 mmol), and the solution was stirred at 80° C. for 3 h. After the reaction finished, the solvent was concentrated in vacuo, and extracted with 1N-HCl and EtOAc. The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (eluent: EtOAc/Hex=1/4) to give the title compound (147 mg, 89%).

Provenance & Evidence