Ammonium Chloride → HCID 72192936, Verbindung

To a stirred solution of compound 3 (0.075 g, 0.24 mmol, 1.0 equiv) in methanol (3 mL) was added zinc powder (0.0800 g, 1.22 mmol, 5.00 equiv) followed by ammonium chloride solution (0.065 g, 1.2 mmol, 5.0 equiv) in water (1 mL). The reaction mixture was stirred at RT for 4 h. After consumption of the starting material (by TLC), the reaction mixture was diluted with DCM (10 mL), water (10 mL) and filtered through a pad of celite. The organic layer was separated from filtrate and the aqueous layer was extracted with DCM (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, concentrated under vacuum to give crude; which was purified by silica gel column chromatography (EtOAc/Hexane, 1:4) to afford compound 2A (0.050 g, 71%) as an off-white solid. TLC: 40% EtOAc/Hexane (Rf: 0.20); 1H NMR (400 MHz, CDCl3): δ 7.32-7.29 (m, 2H), 7.04 (t, J=8.8 Hz, 2H), 5.84 (d, J=9.6 Hz, 1H), 5.78 (s, 1H), 4.25-4.18 (m, 4H), 4.04-3.96 (m, 3H), 1.30 (t, J=6.8 Hz, 3H); LC-MS: m/z=322 (M++1) at RT 3.38 (99.0% purity); UPLC purity: 99.5%.

1. customAfter consumption of the starting material (by TLC)
2. additionthe reaction mixture was diluted with DCM (10 mL), water (10 mL)
3. filtrationfiltered through a pad of celite
4. customThe organic layer was separated from filtrate
5. extractionthe aqueous layer was extracted with DCM (2×10 mL)
6. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
7. concentrationconcentrated under vacuum
8. customto give crude
9. customwhich was purified by silica gel column chromatography (EtOAc/Hexane, 1:4)

ORD-Eintrag

ord-95d8b0c810914bf88d1941e8747f0cb0

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08916133B2