Water → HCID 131732898, compound

Bromotrimethylsilane (0.46 mL, 3.5 mmol) was added to a stirred solution of 7a (0.57 g, 1.4 mmol) in dry CH2Cl2 at 20° C., and stirring was continued for 18 h. Water (5 mL) was added, and the mixture was stirred vigorously for 30 min. The aqueous layer was removed, and the organic phase was extracted again with H2O (5 mL). Freeze-drying of the combined aqueous phase provided the hydrobromide salt 7b as a colorless solid (0.54 g, 99%), which was used without further purification. A sample was crystallized from CH2Cl2-hexane: mp 79-81° C.; IR (neat) νmax 3275, 2980, 1640, 1515, 1235, 830 cm−1; 1H NMR (CD3OD, 300 MHz) δ 6.95 (d, J=8.4 Hz, 2H), 6.60 (d, J=8.4 Hz, 2H), 3.47 (m, 1H), 3.41 (s, 3H), 3.25-3.02 (m, 5H), 2.72-2.62 (m, 2H), 2.33 (m, 1H), 1.88-1.76 (m, 2H), 1.72-1.64 (m, 2H), 1.13 (d, J=7.2 Hz, 3H); 13C NMR (CD3OD, 125.5 MHz) δ 175.6, 157.0, 131.0, 130.8, 116.2, 81.6, 62.9, 61.8, 46.5, 45.5, 41.3, 35.2, 24.1, 23.9, 15.5; HRMS (APCI) m/z 307.2026 [(M−HBr)+H]+ (calcd for C17H27N2O3, 307.2022).

1. stirringthe mixture was stirred vigorously for 30 min
2. customThe aqueous layer was removed
3. extractionthe organic phase was extracted again with H2O (5 mL)
4. customFreeze-drying of the combined aqueous phase

ORD record

ord-1a048fcc28854e0a9785fa6453a8f1bb

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09044518B2