2-Bromopentane → 2-(2-(1-(3-(Pentan-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetic acid

Participants

Reaction Steps

The title compound was prepared by an analogous sequence to that used to synthesize Example 51 from 7F (tert-butyl 2-(2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate) except that 2-bromopentane instead of (bromomethyl)cyclobutane was used as the alkylating agent. The crude product was purified by preparative LC/MS (Column: Waters XBridge C18, 19×200 mm, 5-μm particles; Mobile Phase A: 5:95 MeCN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 MeCN:water with 10 mM NH4OAc; Gradient: 30-70% B over 20 min, then a 5-min hold at 100% B; Flow rate: 20 mL/min) to give the title compound (11.5 mg, 88% yield; 96% purity by LC/MS) as a light yellow oil. LCMS, [M−H]−=375. 1H NMR (500 MHz, DMSO-d6) δ 7.96 (s, 1H), 7.17 (t, J=8.0 Hz, 1H), 6.96-6.83 (m, 2H), 6.74 (d, J=8.3 Hz, 1H), 4.41 (sxt, J=5.9 Hz, 1H), 3.95 (s, 2H), 3.76 (s, 2H), 3.50 (t, J=6.7 Hz, 3H), 2.09-1.96 (m, 2H), 1.87-1.75 (m, 2H), 1.71-1.57 (m, 5H), 1.56-1.47 (m, 1H), 1.46-1.32 (m, 3H), 1.21 (d, J=6.1 Hz, 3H), 0.90 (t, J=7.2 Hz, 3H).

Provenance & Evidence