Trifluoromethanesulfonic acid → HCID 72724108, compound

Participants

Reaction Steps

By a procedure similar to that for 11a, the reaction of alcohol 10b (498 mg, 1.5 mmol) with 3-pentyl trichloroacetimidate (420 mg, 1.8 mmol) in the presence of CF3SO3H (15.6 μL, 0.18 mmol), followed by another batches of the imidate and CF3SO3H, gave the alkylation product 11b (495 mg, 82% yield). Colorless oil; TLC (EtOAc/hexane, 1:1) Rf=0.2; [α]D20=−61.3 (c=0.65, CDCl3); IR (neat) 2100, 1756, 1634, 1246 cm−1; 1H NMR (600 MHz, CDCl3) δ 6.56 (1 H, d, JP-2=21.6 Hz), 5.71 (1 H, d, J=6.9 Hz), 4.52 (1 H, d, J=7.8 Hz), 4.34-4.30 (1 H, m), 4.11-4.01 (4 H, m), 3.31-3.23 (2 H, m), 2.69-2.64 (1 H, m), 2.12-2.08 (1 H, m), 2.01 (3 H, s), 1.51-1.43 (4 H, m), 1.39-1.31 (6 H, m), 0.90-0.81 (6 H, m); 13C NMR (150 MHz, CDCl3) δ 171.0, 141.7, 126.3 (C-1, d, JP-1=182 Hz), 810.9, 73.7, 62.14, 62.10, 54.3, 57.1, 31.0, 26.2, 25.4, 23.6, 16.4, 16.3, 9.6, 9.2; 31P NMR (162 MHz, CDCl3) δ 16.99; HRMS calcd for C17H32N4O5P (M++H): 403.2110, found: m/z 403.2111.

Provenance & Evidence