4-Pyridin-2-ylbenzaldehyde → (4-(Piperidin-2-yl)phenyl)methanol

To a solution of 4-pyridin-2-yl-benzaldehyde (1.036 g, 5.65 mmol) in EtOH (95%, 3.1 mL) and conc. HCl (0.48 mL) in a Parr hydrogenation flask was added PtO2 (57 mg, 0.251 mmol) and the mixture hydrogenated at 50 psi H2 for 40 h. The mixture was filtered through celite, the cake washed with MeOH and the solvent was removed from the eluent under reduced pressure. The resultant yellow solid was dissolved in 1 N NaOH (30 mL) and extracted with ether (4×50 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated under reduced pressure to give crude 1-(hydroxymethyl)-4-(piperidin-2-yl)-benzene (0.98 g) as white solid. To a solution of the solid in THF (25 mL), triethylamine (10 drops) and water (10 drops) was added di-tert-butyl dicarbonate (1.51 g, 6.92 mmol) and the reaction stirred at room temperature for 20 h. The mixture was concentrated under reduced pressure and the residue taken up in CH2Cl2 (100 mL) and washed with brine (3×75 mL). The organic phase was dried (Na2SO4), filtered and concentrated under reduced pressure to give crude 1-(hydroxymethyl)-4-[(1-butoxycarbonyl)-piperidin-2-yl]-benzene (1.87 g) as an oil.

1. filtrationThe mixture was filtered through celite
2. washthe cake washed with MeOH
3. customthe solvent was removed from the eluent under reduced pressure
4. dissolutionThe resultant yellow solid was dissolved in 1 N NaOH (30 mL)
5. extractionextracted with ether (4×50 mL)
6. dry with materialThe combined organic phases were dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORDレコード

ord-5953b38797a94f048008796da7f74c46

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07091217B2