Triethylamine → HCID 86623621, compound

To a solution of (2E-)-(5-methoxy-4-methyl-2,3-dihydro-1H-inden-1-ylidene)acetic acid (1.0 g, 4.58 mmol, from Step F) in methanol (10 mL) was added [(S)-(−)-2,2′bis(diphenylphosphino)-1,1′-binaphthyl]ruthenium (II) (36.0 mg, 0.0458 mmol) and triethylamine (64 μL, 0.458 mmol). The resultant mixture was subjected to 3 atm H2 and was shaken at ambient temperature for 24 hr. The reaction mixture was filtered through Celite®, and concentrated in vacuo. The residue was dissolved in THF (5 mL) and methanol (5 mL) and treated with TMSCHN2 (6.51 mL, 13.0 mmol) at ambient temperature. After 1 hr, the reaction mixture was concentrated in vacuo and purified by flash chromatography (3% EtOAc/hexanes) on SiO2 to give 828 mg of the title compound as a colorless liquid: 1H NMR (500 MHz, CDCl3) δ 1.71-1.78 (m, 1H), 2.15 (s, 3H), 2.37-2.46 (m, 2H), 2.73-2.81 (m, 2H), 2.86-2.92 (m, 1H), 3.53-3.59 (m, 1H), 3.73 (s, 3H), 3.82 (s, 3H), 6.69 (d, 1H, J=8.2 Hz), 6.96 (d, 1H, J=8.2 Hz).

1. filtrationThe reaction mixture was filtered through Celite®
2. concentrationconcentrated in vacuo
3. dissolutionThe residue was dissolved in THF (5 mL)
4. waitAfter 1 hr
5. concentrationthe reaction mixture was concentrated in vacuo
6. custompurified by flash chromatography (3% EtOAc/hexanes) on SiO2

ORD record

ord-c46fbcf48cdb48b7a699b3404c460b5c

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07605171B2