Methanol → HCID 57697447, compound

Temperature

90 °C

To a solution of the compound (2.40 g) obtained in step 5 in THF (30 mL) was added 1M BH3.THF complex/THF solution (41.5 mL) was added at 0° C., and the mixture was stirred at 90° C. for 1 hr. After the reaction mixture was cooled to 10° C., MeOH (10 mL) was added, and the mixture was concentrated under reduced pressure. The residue was suspended in MeOH (15 mL) and 6N hydrochloric acid (15 mL), and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was cooled to 10° C., and made basic with aqueous sodium hydroxide solution, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine, and concentrated. The residue was purified by silica gel column chromatography (solvent; 5% ethyl acetate/hexane) to give the title compound (1.80 g, 79%) as a colorless oil.

1. additionwas added at 0° C.
2. temperatureAfter the reaction mixture was cooled to 10° C.
3. concentrationthe mixture was concentrated under reduced pressure
4. stirring6N hydrochloric acid (15 mL), and the mixture was stirred at 80° C. for 1 hr
5. temperatureThe reaction mixture was cooled to 10° C.
6. extractionthe resultant product was extracted with ethyl acetate
7. washThe organic layer was washed with brine
8. concentrationconcentrated
9. customThe residue was purified by silica gel column chromatography (solvent; 5% ethyl acetate/hexane)

ORD record

ord-681161712300432d9f1cd370aa02a12d

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158617B2