tert-Butyl acetate → HCID 68295612, compound

Participants

Reaction Steps

A solution of (S)-3-(2-((tert-butyldiphenylsilyl)oxy)-1-hydroxyethyl)-4-(8-fluoro-5-methylchroman-6-yl)-2-methylisoquinolin-1(2H)-one (92 mg, 0.148 mmol) in tert-butyl acetate (1994 μl, 14.80 mmol) was treated with 2 drops of 70% perchloric acid. After 18 h, the reaction mixture was poured into sat. aq. NaHCO3 and extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by ISCO (0-30% EtOAc-hexanes) to afford (S)-3-(1-(tert-butoxy)-2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-(8-fluoro-5-methylchroman-6-yl)-2-methylisoquinolin-1(2H)-one (49 mg, 0.072 mmol, 48.9% yield) as a white foam: 1H NMR (400 MHz, CHLOROFORM-d) δ=8.45 (dd, J=1.5, 7.7 Hz, 1 H), 7.70-7.63 (m, 2 H), 7.63-7.56 (m, 2 H), 7.41 (none, 8 H), 6.89 (d, J=11.3 Hz, 1 H), 6.85-6.78 (m, 1 H), 4.83 (dd, J=2.0, 7.4 Hz, 1 H), 4.30 (t, J=5.2 Hz, 2 H), 3.88 (dd, J=7.5, 10.6 Hz, 1 H), 3.82 (s, 3 H), 3.58 (dd, J=2.0, 10.7 Hz, 1 H), 2.73-2.52 (m, 2 H), 2.20-2.07 (m, 2 H), 1.64 (s, 3 H), 1.16 (s, 9 H), 0.98 (s, 9 H); LC/MS (m/z) ES+=678 (M+1).

Provenance & Evidence