Methanol → HCID 15462816, compound

Temperature

5 °C

In a 2-L three-neck flask, the product of step (2) (100.00 g) was dissolved in tetrahydrofuran (500 ml) by using a stirrer and cooled on a water bath so that the inside temperature became 2-3° C. To the resultant solution, a borane-tetrahydrofuran complex—1 M tetrahydrofuran solution (532 ml) was added by using a syringe. After stirring for one hour at 5° C., the mixture was further stirred for four hours at room temperature, to thereby obtain an almost colorless reaction mixture. The reaction mixture was cooled again on a water bath, and methanol (100 ml) was added gradually thereto by using a pipette, to dissolve the excessive borane-tetrahydrofuran complex. After completion of hydrogen gas generation, the reaction mixture was removed from the water bath and stirred for one hour during the temperature was returned to room temperature. Extremely small quantities of impurities such as fibers of filter were removed through suction-filtered and the solvent was removed under reduced pressure. To the residue was added methanol (300 ml) before drying, to thereby crystallize the residue. About one half in volume of methanol was removed under reduced pressure, to thereby yield a colorless mud-like product. The product was added to water (1 L) and the resultant solution was stirred. Crystals in the solution were suction-filtered, washed with water, and air-dried for three days, to thereby yield the target product (97.12 g). This product was submitted directly to the next reaction without further purification.

1. temperaturecooled on a water bath so that the inside temperature
2. custombecame 2-3° C
3. stirringthe mixture was further stirred for four hours at room temperature
4. customto thereby obtain an almost colorless reaction mixture
5. temperatureThe reaction mixture was cooled again on a water bath
6. dissolutionto dissolve the excessive borane-tetrahydrofuran complex
7. customAfter completion of hydrogen gas generation, the reaction mixture was removed from the water bath
8. stirringstirred for one hour during the temperature
9. customwas returned to room temperature
10. filtrationExtremely small quantities of impurities such as fibers of filter
11. customwere removed
12. filtrationthrough suction-filtered
13. customthe solvent was removed under reduced pressure
14. additionTo the residue was added methanol (300 ml)
15. custombefore drying
16. customto thereby crystallize the residue
17. customAbout one half in volume of methanol was removed under reduced pressure
18. customto thereby yield a colorless mud-like product
19. filtrationCrystals in the solution were suction-filtered
20. washwashed with water
21. customair-dried for three days

ORD record

ord-220dec1393794568851ad9801eb6b087

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06403607B1