Hydrochloric Acid → HCID 57038928, compound

Temperature

-78 °C

To a stirring solution of the methyl ester from Example 9, Step B (1.2 mmol, 330 mg) in 10 mL of DCM cooled to −78° C. was added dropwise over 20 min. diisobutylaluminum hydride (2.4 mmol, 2.4 mL of 1 M solution in DCM). The solution was stirred at −78° C. for 2 h. Methanol (2 mL) cooled to −78° C. was canulated dropwise to the reaction mixture over 5 min. After 10 min. the reaction was allowed to warm to room temperature, during which time a white precipitate formed. DCM (30 mL) was added, and the solution was poured into 2 N HCl (50 mL). The organic phase was collected and the aqueous phase was extracted with DCM (2×25 mL). The combined organic phase was dried with MgSO4 and the solvent removed under reduced pressure. The oily residue was dissolved in DCM and passed through a silica plug eluting with DCM. Removal of solvent under reduced pressure afforded the title compound as a clear oil. MS(ESI): m/z 250 (M+H). HPLC B: 1.31 min.

1. waitwas canulated dropwise to the reaction mixture over 5 min
2. waitAfter 10 min. the reaction was allowed
3. temperatureto warm to room temperature, during which time a white precipitate
4. customformed
5. customThe organic phase was collected
6. extractionthe aqueous phase was extracted with DCM (2×25 mL)
7. dry with materialThe combined organic phase was dried with MgSO4
8. customthe solvent removed under reduced pressure
9. dissolutionThe oily residue was dissolved in DCM
10. washeluting with DCM
11. customRemoval of solvent under reduced pressure

ORD record

ord-9d3cf9b7c8754e54acefd994e0788bea

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06511994B2