Aluminium lithium hydride → HCID 21842589, compound

A suspension of 4-(N-methylcarbamoyl)-3-phenylbutyric acid (250 mg, 1.13 mmol) in 5.0 mL of THF was stirred in an ice bath as a 1.0 M solution of LAH (4.5 mL, 4.5 mmol) in THF was added dropwise over 10 min. The mixture was stirred 1 h at room temperature followed by 3 h at reflux. The reaction was then cooled in the ice bath and quenched with 0.70 mL of saturated aqueous Rochelle salt. The resulting precipitate was filtered and washed with 100 mL of ethyl acetate, and the combined filtrates were concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with 10-15% methanol in dichloromethane containing 1% ammonium hydroxide, to give 151 mg of the title compound as a viscous oil. 1NMR (400 MHz, CD3OD): δ 7.32-7.26 (m, 2H), 7.22-7.16 (m, 3H), 3.45-3.32 (m, 2H). 2.80-2.70 (m, 1H), 2.44 (ddd, 1H, J=12, 10, 6 Hz), 2.32 (ddd, 1H, J=12, 10, 6 Hz), 2.28 (s, 3H), 1.94-1.74 (m, 4H). Mass spectrum (NH3 /CI): m/z=194 (M+1).

1. additionwas added dropwise over 10 min
2. waitfollowed by 3 h
3. temperatureat reflux
4. customquenched with 0.70 mL of saturated aqueous Rochelle salt
5. filtrationThe resulting precipitate was filtered
6. washwashed with 100 mL of ethyl acetate
7. concentrationthe combined filtrates were concentrated under reduced pressure
8. customThe residue was purified by flash column chromatography on silica gel
9. washeluting with 10-15% methanol in dichloromethane containing 1% ammonium hydroxide

ORD record

ord-9d2e738d1d8a4b2bb9c6c4d549b3a522

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05962462