Ammonium Chloride → HCID 22473218, compound

Participants

Reaction Conditions

Reaction Steps

A solution of BuLi (9.94 mmol) in hexanes (1.6 M, 6.2 ml) was added dropwise over 3 min to a stirred solution of 2-bromo-5-(tert-butyldimethylsilyloxymethyl)pyridine (2.0 g, 6.63 mmol) in THF (40 ml) at −78° C. under N2. The resulting solution was then stirred at −78° C. for 30 min and a solution of N-Boc-4-piperidone (1.95 g, 9.93 mmol) in THF (20 ml) was added. The reaction was allowed to warm to room temperature and stirred for a further 15 min. NH4Cl solution (40 ml) was added and the organics were extracted with EtOAc (3×50 ml). The combined organics were washed with brine (50 ml) and then concentrated under reduced pressure. A solution of tetrabutylammonium fluoride(6.63 mmol) in THF (1.0 M, 6.63 ml) was added to a stirred solution of the crude silyl ether in THF (100 ml) at room temperature under N2 and the reaction mixture was stirred for 1 h. NH4Cl solution (40 ml) was added and the organic were extracted with EtOAc (3×50 ml), then washed with brine (50 ml), dried and concentrated under reduced. The mixture was purified by column chromatography on silica using 100% EtOAc as eluent to yield the desired hydroxymethylpyridine (0.89 g, 44%). 1H NMR (360 MHz, CDCl3) δ 8.48 (1H, s), 7.74 (1H, d, J=8.1 Hz), 7.32 (1H, d, J=8.1 Hz), 4.72 (1H, broad s), 4.10 (2H, s), 4.10-4.00 (2H, m), 3.30-3.20 92H, m), 1.89 (2H, td, J=8.1, 4.9 Hz), 1.56 92H, d, J=8.1 Hz), 1.47 (9H, s). m/z (ES+) 423 (M+H+).

Provenance & Evidence