反应详情

R2-ether formation: To a slurry of sodium hydride (60% in mineral oil, 2.75 g) in DMSO (100 ml) were added (2S,4R)-[4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-methanol (11.2 g) in portions within 0.5 h and benzyl bromide (7.2 ml) dropwise within 0.5 h at 20° C. The reaction mixture was stirred at room temperature for 1.5 h, poured onto ice/water and extracted with EtOAc. The organic phases were washed with water and brine, dried over magnesium sulphate and concentrated. The residue was crystallized from acetone/Et2O/hexane to obtain (2S,4R)-2-benzyloxymethyl-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine (10.05 g) as a colorless solid, mp 101-103° C., MS: 454 (MH+).

1. additionpoured onto ice/water
2. extractionextracted with EtOAc
3. washThe organic phases were washed with water and brine
4. dry with materialdried over magnesium sulphate
5. concentrationconcentrated
6. customThe residue was crystallized from acetone/Et2O/hexane