Hydrochloric Acid → HCID 68524570, compound

To a solution of 6-bromo-pyridin-3-ol (5.0 g, 28.7 mmol) in anhydrous THF (75 mL) and anhydrous toluene (40 mL) at −78° C. was added n-butyllithium (2.5 M in hexane, 28.73 mmol). The mixture was stirred for 20 min. A solution of sec-butyllithium (1.4 M in cyclohexane, 43.1 mmol) was added dropwise and the mixture stirred at −78° C. for 1 hour. To the mixture was added cyclohexanone (4.23 g, 43.1 mmol) in THF (25 mL) at −78° C. and the mixture stirred at −78° C. for 1 hour. Saturated NaH2PO4 solution (10 mL) was slowly added to the mixture and the mixture then warmed to room temperature. Water (300 mL) was added. The reaction mixture was neutralized with hydrochloric acid (2N), and the mixture extracted three times with EtOAc. The organic layer was washed with brine and dried (Na2SO4). Silica gel chromatography (EtOAc/heptane) provided 2.63 g of the title compound. C11H15NO2 (193.11), LCMS (ESI): 194.09 (M++H).

1. stirringthe mixture stirred at −78° C. for 1 hour
2. stirringthe mixture stirred at −78° C. for 1 hour
3. extractionthe mixture extracted three times with EtOAc
4. washThe organic layer was washed with brine
5. dry with materialdried (Na2SO4)

ORD record

ord-86efa231545948d5a42a96a767f81146

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642603B2