Hydroxylamine → Allyl Fmoc Alcohol

Participants

Reaction Steps

9-Fluorenylmethyl chloroformate (5.65 g, 0.022 mol) was added portionwise to a stirred solution of the amino alcohol 4 (7.5 g, 0.02 mol) and Na2CO3 (5.26 g, 0.05 mol) in a mixture of THF (150 ml) and water H2O (150 ml) at 0° C. The reaction mixture was allowed to return to room temperature, stirred for a further 2 h, and then extracted with EtOAc (3×50 ml). The combined organic phase was washed with H2O (3×50 ml) and brine (3×25 ml), dried over magnesium sulphate and evaporated in vacuo to give a dark red oil. This was purified by flash column chromatography (petroleum ether 40-60/EtOAc, 1:1) to afford 5b as a pale yellow oil (8.11 g, 68%): 1H NMR (270 MHZ, CDCl3): δ 1.72-2.18 (m, 6H); 2.9 (t, J=6.4, 2H); 3.43-3.91 (m, 3H); 3.81 (s, 3H); 4.25-4.54 (m, 5H); 4.61-4.65 (m, 2H); 5.21-5.37 (m, 2H); 5.85-6.0 (m, 1H); 6.85 (s, 1H); 7.31-7.79 (m, 9H); 8.77 (br s, 1H); 13C NMR (67.8 MHZ, CDCl3): δ 25.1, 28.4, 35.3, 47.0, 56.7, 60.9, 64.3, 65.4, 66.3, 67.1, 106.4, 111.7, 118.3, 120.0, 125.2, 127.1, 127.2, 127.8, 131.5, 131.9, 141.3, 143.7, 144.4, 150.2, 153.8, 170.3; MS (FAB): 601 (M+.+1); HRMS: calcd for C34H36N2O8 600.667, found 600.2175. IR (film): ν 3315, 2952, 1727, 1597, 1522, 1452, 1392, 1322, 1174, 1117, 1017.

Provenance & Evidence