Tetrabutylammonium Fluoride → HCID 70171848, compound

Participants

Reaction Steps

To a stirred solution of (5Z,10S)-(−)-N-tert-butoxycarbonyl-N-[2-tert-butyldimethylsilyloxyethyl]-10-amino-5-undecenoic acid benzyl ester (8) (100 mg, 0.18 mmol) in 1 mL of THF was added 0.2 mL of a 1M THF solution of tetrabutylammonium fluoride. The mixture was stirred at rt for 16 h, then concentrated, and purified by flash chromatography (11 mm×6″ column, eluted with 20% v/v EtOAc/hexane) yielding 76 mg of the title compound (9) as a colorless oil (0.17 mmol, 97% yield). 1H NMR (conformeric mixture, 500 MHz, C6D6): δ7.23-7.20 (m, 1H, ArH), 7.13-6.98 (m, 4H, ArH), 5.39-5.33 (m, 1H, RCH═CHR′), 5.32-5.26 (m, 1H, RCH═CHR′), 5.01 (s, 2H, ArCH2O2CR), 3.85-3.78 (m, 0.5H, NCHCH3), 3.76-3.50 (m, 2.5H, NCHCH3 and OCH2CH2N), 3.21-3.00 (m, 2H, OCH2CH2N), 2.15 (t, J=7.3 Hz, 2H, RO2CCH2), 2.01-1.90 (m, 4H, CH2CH═CHCH2), 1.63 (p, J=7.3 Hz, 2H, RO2CCH2CH2), 1.42 (s, 9H, Boc), 1.31-1.20 (m, 3H, CHaHbCH2CHN), 1.16-1.05 (m, 1H, CHaHbCH2CHN), 0.93-0.82 (m, 3H NCHCH3).

Provenance & Evidence