Chloroform → benzyl (RS)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropylcarbamate

Participants

Reaction Steps

Camphorsulfonic acid (0.069 g, 0.296 mmol) was added to a solution of benzyl ((5R/S,6R/S)-6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)methylcarbamate (1.83 g, 5.92 mmol) in acetone (50 mL) and the solution was stirred at RT. After 40 mins chloroform was added and the solution was washed with aq NaHCO3 and then processed normally. Chromatography (EtOAc/Hex 1:1, and then 3:1) gave firstly benzyl (RS)-2-((RS)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropylcarbamate (0.86 g, 2.78 mmol, 47.0% yield) and then benzyl ((4RS,5RS)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-5-yl)methylcarbamate (0.942 g, 3.05 mmol, 51.5% yield) as syrups; compound 10.3 13C NMR (CDCl3) δ 157.6, 136.8, 128.9, 128.6, 128.5, 109.3, 76.4, 68.0, 67.3, 61.3, 44.3, 39.9, 26.9, 25.7; compound 10.4 13C NMR (CDCl3) δ 157.1, 136.8, 128.9, 128.6, 128.5, 99.0, 72.5, 69.1, 67.3, 64.2, 62.3, 40.3, 36.7, 29.1, 20.2.

Provenance & Evidence