Trifluoroacetic acid → HCID 22744553, compound

To a stirred solution of 7-oxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (100 mg, 0.41 mmol) in MeOH (5 mL) was added NaBH4 (47 mg, 1.24 mmol) in one portion at room temperature. The mixture was stirred at room temperature overnight, and then quenched with sat. NaHCO3. The mixture was extracted with EtOAc (20 mL) three times. The organic layer was washed with sat. NaHCO3 and brine (20 mL) respectively. The organic layer was dried over Na2SO4, and then filtered. The solvent was concentrated under reduced pressure to give a crude product La, which was dissolved in CH2Cl2 (5 mL). Trifluoroacetic acid (2 mL) was added to the solution dropwise at 0° C. After being stirred at room temperature for 2 hours, the mixture was concentrated under reduced pressure. The residue was further dried on high-vacuum to give 3-oxa-9-aza-bicyclo[3.3.1]nonan-7-ol (Compound L) which was directly used for next step. MS: calc'd (MH+) 144, measured (MH+) 144.

1. customquenched with sat. NaHCO3
2. extractionThe mixture was extracted with EtOAc (20 mL) three times
3. washThe organic layer was washed with sat. NaHCO3 and brine (20 mL) respectively
4. dry with materialThe organic layer was dried over Na2SO4
5. filtrationfiltered
6. concentrationThe solvent was concentrated under reduced pressure
7. customto give a crude product La, which
8. stirringAfter being stirred at room temperature for 2 hours
9. concentrationthe mixture was concentrated under reduced pressure
10. customThe residue was further dried on high-vacuum

ORD record

ord-2164b78070c34939a018af390ea6ea6b

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266904B2