HCID 12036867, compound → HCID 67020382, compound

2-Propionyl-(6-methyl-6-azabicylo[3.2.2]non-2-ene) [22] A flask was charged with LiAlH4 (410 mg, 10.8 mmol) and dry THF (20 mL), giving a slurry. A solution of 21 (645 mg, 2.15 mmol) in dry THF (30 mL) was added dropwise with stirring, and the reaction was then heated to reflux for 1 h. The reaction was cooled to room temperature, and quenched with dropwise addition of 50 mL EtOAc. The reaction was diluted with H2O (40 mL) and NaCl (sat, aq, 40 mL), and the layers separated. The aqueous layer was extracted with 2×40 mL EtOAc. The organic layers were combined and extracted with 3×50 mL 10% HCl. The aqueous layers were then combined and neutralized with NaHCO3(s) and basified to pH=12 with NaOH (aq). The aqueous layer was extracted with 3×50 mL CH2Cl2, and the organic layers combined, dried (MgSO4), and evaporated to give 2-(1-hydroxy-1-propyl)-(6-methyl-6-azabicyclo[3.2.2]non-2-ene) as a yellow oil (1:1 ratio of diastereomers). Crude yield: 419 mg, 2.17 mmol, 100%).

1. customgiving a slurry
2. temperaturethe reaction was then heated
3. temperatureto reflux for 1 h
4. customquenched with dropwise addition of 50 mL EtOAc
5. additionThe reaction was diluted with H2O (40 mL) and NaCl (sat, aq, 40 mL)
6. customthe layers separated
7. extractionThe aqueous layer was extracted with 2×40 mL EtOAc
8. extractionextracted with 3×50 mL 10% HCl
9. extractionThe aqueous layer was extracted with 3×50 mL CH2Cl2
10. dry with materialdried (MgSO4)
11. customevaporated

ORD record

ord-f777bfee09d0488f9cc7d5ea46772685

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550588B2