Diisobutylaluminumhydride → HCID 59232105, compound

To a cooled (0° C.) solution of the product of step 4 of Example 96 (220.0 mg, 0.68 mmol) in THF (23 mL) was added diisobutylaluminum hydride (1 M in THF, 7.4 mL, 7.4 mmol). The mixture was allowed to warm to rt and stirred for 30 min. The reaction was cooled (0° C.) and quenched with methanol (1 mL). The mixture was poured into a vigorously stirred 1.2 M aqueous Rochelle's salt solution (50 mL). The resultant mixture was stirred for 30 min and then extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried over sodium sulfate and concentrated to dryness under reduced pressure. The crude material was purified by HPLC using a gradient of 50-90% MeCN in water to yield 170.0 mg (99%) of the desired product containing trace impurities. 1H-NMR (DMSO-d6) δ 8.14 (s, 1H), 7.38 (d, J=8.0 Hz, 2H), 7.07 (d, J=8.0 Hz, 2H), 6.76 (s, 1H), 4.75 (s, 2H); MS [M+H]+=256.2; LCMS RT=1.05 min.

1. temperatureThe reaction was cooled (0° C.)
2. customquenched with methanol (1 mL)
3. additionThe mixture was poured into a vigorously stirred 1.2 M aqueous Rochelle's salt solution (50 mL)
4. stirringThe resultant mixture was stirred for 30 min
5. extractionextracted with ethyl acetate (3×50 mL)
6. dry with materialThe combined organic extracts were dried over sodium sulfate
7. concentrationconcentrated to dryness under reduced pressure
8. customThe crude material was purified by HPLC

ORD record

ord-25aee3952da842f991444d1ab50546e4

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129379B2