Hydrochloric Acid → HCID 11369807, compound

Tetrabutylammonium fluoride (0.25 mL, 0.25 mmol, 1.0 M commercial solution in THF) was added to a solution of silyl ether VII (95 mg, 0.23 mmol) in 2 mL of dry THF under an argon atmosphere and at 0° C. After stirring for 30 minutes at said temperature, it was acidulated with 10% HCl and the organic phase was extracted with dichloromethane (3×15 mL). The pooled organic phase was dried (Na2SO4 anh.), filtered and concentrated under reduced pressure. The obtained residue was purified by means of flash chromatography in silica gel (diethyl ether) to give 29 mg of alcohol VIII in a pale yellow oil form (43%). [α]25D−265.5° (c 1.2 in CHCl3); 1H-NMR (250 MHz, CDCl3, δ) 8.22 (d, 2H, J 8.7), 7.51 (d, 2H, J 8.7), 6.17 (d, 1H, J 9.8), 5.82 (ddd, 1H, J 9.8, 3.3 and 1.0), 4.81 (m, 1H), 4.78 (s, 2H), 4.02 (t, 1H, J 3.3), 3.35 (broad s, 1H) and 2.44 (m, 2H); 13C-NMR (63 MHz, CDCl3, δ) 177.2, 147.6, 144.8, 137.4, 127.7, 125.1, 123.8, 74.5, 73.4, 72.2, 71.0 and 36.9; IR (NaCl)/cm−1 3405 and 1784; EM-IQ+ (m/z) 292 (MH+); HRMS calculated for C14H14O6N (MH+): 292.0821, 292.0826 found.

1. extractionthe organic phase was extracted with dichloromethane (3×15 mL)
2. dry with materialThe pooled organic phase was dried (Na2SO4 anh.)
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe obtained residue was purified by means of flash chromatography in silica gel (diethyl ether)

ORD record

ord-bb79b34b1520437c96131022f9c0ac6d

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07563896B2