Hydrochloric Acid → HCID 22178188, compound

Optically active 4-cyano-3-hydroxy-4-methylpentanoic acid (1.5 g, 9.54 mmol) was dissolved in dry THF (5 mL) and a solution (38.175 mmol) of borane-THF complex was gradually added dropwise thereto at 0° C. After the completion of the dropwise addition, the mixture was stirred at room temperature for 3 hr and then 2N aqueous hydrochloric acid solution was added to neutralize the reaction mixture. Ethyl acetate (20 mL) was added thereto and the mixture was stirred vigorously. An organic layer was extracted. Ethyl acetate (20 mL) was further added to an aqueous layer and the mixture was stirred vigorously. The organic layer was extracted again. This step was repeated 3 times and the obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give optically active 4-cyano-4-methyl-3-hydroxy-1-pentanol (847 mg, 5.915 mmol) (yield relative to optically active 4-cyano-3-hydroxy-4-methylpentanoic acid: 62%).

1. additiona solution (38.175 mmol) of borane-THF complex was gradually added dropwise
2. customat 0° C
3. additionAfter the completion of the dropwise addition
4. stirringthe mixture was stirred vigorously
5. extractionAn organic layer was extracted
6. additionEthyl acetate (20 mL) was further added to an aqueous layer
7. stirringthe mixture was stirred vigorously
8. extractionThe organic layer was extracted again
9. dry with materialthe obtained organic layer was dried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure

ORD record

ord-db9a64947ba448acac6837ae59b832ee

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06730803B2