Hydrochloric Acid → HCID 86646120, compound

Sodium hydride (>63% oil, 2.09 g, 55 mmol) was added to a solution of ethyl 3-oxohexanoate (7.91 g, 50 mmol) in tetrahydrofuran (50 mL) under ice cooling, and the mixture was stirred in this state for 10 minutes. To the reaction solution, n-butyllithium (1.58 M solution in hexane, 34.8 mL, 55 mmol) was added dropwise, and the mixture was further stirred for 10 minutes under ice cooling. Then, allyl bromide (4.7 mL, 55 mmol) was added thereto, and the mixture was stirred in this state for 1 hour and then further stirred at room temperature for 4 hours. To the reaction solution, 1 N hydrochloric acid and a saturated aqueous solution of ammonium chloride were added, followed by extraction with n-pentane. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was dissolved in ethanol (80 mL). To the solution, sodium borohydride (1.51 g, 40 mmol) was added under ice cooling, and the mixture was stirred in this state for 2 hours. 1 N hydrochloric acid (50 mL) was added thereto, and the mixture was stirred for 30 minutes. Then, saturated saline was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the compound of interest as a pale yellow oil substance (3.64 g, 37%, mixture of diastereomers).

1. stirringthe mixture was further stirred for 10 minutes under ice cooling
2. stirringthe mixture was stirred in this state for 1 hour
3. stirringfurther stirred at room temperature for 4 hours
4. extractionfollowed by extraction with n-pentane
5. washThe organic layer was washed with saturated saline
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. dissolutionThe obtained residue was dissolved in ethanol (80 mL)
9. stirringthe mixture was stirred in this state for 2 hours
10. stirringthe mixture was stirred for 30 minutes
11. additionThen, saturated saline was added
12. extractionfollowed by extraction with ethyl acetate
13. washThe organic layer was washed with saturated saline
14. dry with materialdried over anhydrous magnesium sulfate
15. distillationthe solvent was distilled off under reduced pressure
16. customThe residue was purified by silica gel column chromatography
17. customto obtain the compound of interest
18. additionas a pale yellow oil substance (3.64 g, 37%, mixture of diastereomers)

ORD record

ord-8eec8d1781cd4ad2ad068ea9c9a6fd01

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206104B2