HCID 86606433, compound → HCID 86606432, compound

Temperature

90 °C

416 g of (5 or 6)-formyl-2-methylbicyclo[2.2.1]heptane-2-carbonitrile (2.55 mol) was dissolved in 200 g THF (tetrahydrofuran), 20 g catalyst, 5% Ru on carbon (Aldrich), was added, and the whole reaction mixture was charged into a 1 L autoclave. The autoclave was heated to 90° C. and pressurized with 1000 psig H2 gas for 12 h while the progress of the reaction was periodically monitored by GC analysis. After venting the reactor, cooling to room temperature, and rinsing with THF, the reaction mixture was filtered though a plug of celite under nitrogen. Solvent was removed from the reaction mixture by rotary evaporation, and the residual oil (388 g) was distilled in vacuo to yield 275 g (1.66 mol) of (5 or 6)-(hydroxymethyl)-2-methylbicyclo[2.2.1]heptane-2-carbonitrile as colorless liquid (65% isolated yield). Boiling point: 93.3° C. at 80 mTorr. The product was pure by GC/MS analysis.

1. customthe whole reaction mixture
2. additionwas charged into a 1 L autoclave
3. temperaturecooling to room temperature
4. washrinsing with THF
5. filtrationthe reaction mixture was filtered though a plug of celite under nitrogen
6. customSolvent was removed from the reaction mixture by rotary evaporation
7. distillationthe residual oil (388 g) was distilled in vacuo
8. customto yield

ORD record

ord-0758d93c83ea44b59e1b07d9b88ac3a2

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07682665B2