Hydrochloric Acid → HCID 19738010, compound

Temperature

0 °C

To a solution of the product from Step A (4.23 g, 27.2 mmol) in methylene chloride (40 mL) which had been degassed under nitrogen and cooled to 0° C. was added m-chloroperbenzoic acid (5.9 g, 24.1 mmol). After stirring for six hours the reaction mixture was filtered and the solvent removed. The residue was dissolved in dry THF (50 mL), cooled in an ice bath, and NaBH4 (1.7 g, 41 mmol) was added followed by allowing the reaction mixture to warm to room temperature with continued stirring for 18 hr. Water (25 mL) was added to the reaction mixture and after the pH was adjusted to 6.0 with 2N HCl it was extracted with ethyl acetate (3×10 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, hexane/ethyl acetate) to provide 1.31 g (25%) of product: mp 79°-81° C.

1. filtrationwas filtered
2. customthe solvent removed
3. dissolutionThe residue was dissolved in dry THF (50 mL)
4. temperaturecooled in an ice bath
5. temperatureto warm to room temperature
6. stirringwith continued stirring for 18 hr
7. extractionwas extracted with ethyl acetate (3×10 mL)
8. dry with materialThe combined extracts were dried (MgSO4)
9. customevaporated to a residue which
10. customwas purified by column chromatography (silica, hexane/ethyl acetate)

ORD record

ord-b218d6976f0a4d85907c7032bdf89288

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05240923