Methanol → HCID 12664736, compound

Borane dimethyl sulfide complex (3.5 mL, 10.0 M in THF) is added to a solution of 2-cyclopentyl-succinic acid 4-tert-butyl ester 1-methyl ester (8.6 g, 35.5 mmol) in 100 mL of THF at 0° C. The mixture is warmed to room temperature overnight, cooled to 0° C., and treated with 50 mL of MeOH. After being warmed to room temperature over 1 hour, the solvents are evaporated, and the oil is dried at room temperature under vacuum for 12 hours. It is taken up in 100 mL of THF containing 0.1 g of pTsOH, and the solution is warmed to reflux for 12 hours. The THF is evaporated under reduced pressure, and remaining oil is taken up in 100 mL of Et2O. The Et2O solution is washed with 2.0N NaOH (3×50 mL) and 50 mL of brine. Drying over MgSO4 followed by evaporation of the solvent gives 4.4 g (80% yield) of 4-cyclopentyl-dihydro-furan-2-one as an oil. NMR (1H, 400 MHz, CDCl3) δ1.1 (2H, m); 1.3-1.8 (7H, m); 2.2 (1H, dd); 1.4 (1H, m); 1.6 (1H, dd); 3.9 (1H, dd); 4.4 (1H, dd).

1. temperaturecooled to 0° C.
2. temperatureAfter being warmed to room temperature over 1 hour
3. customthe solvents are evaporated
4. customthe oil is dried at room temperature under vacuum for 12 hours
5. temperaturethe solution is warmed
6. temperatureto reflux for 12 hours
7. customThe THF is evaporated under reduced pressure
8. washThe Et2O solution is washed with 2.0N NaOH (3×50 mL) and 50 mL of brine
9. dry with materialDrying over MgSO4
10. customfollowed by evaporation of the solvent

ORD record

ord-47bdd0df477a420f8c833063857ee00e

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627771B1