Acetic Acid → HCID 86662313, compound

Participants

Reaction Steps

To a slurry of methoxy azetidine HCL salt (24.2 g, 198 mmol, Eq: 1.00) in 400 mL of methylene chloride was added triethylamine (24.0 g, 33.1 ml, 237 mmol, Eq: 1.2). The precipitate formed went back into solution. Next 6-chloronicotinaldehyde (28 g, 198 mmol, Eq: 1.00) and acetic acid (22.6 ml, 396 mmol, Eq: 2.0) was added. Finally sodium triacetoxyhydroborate (41.9 g, 198 mmol, Eq: 1.00) was added in portions. The first 11 g were added and waited for the chunks to disperse. The second 11 g were then added and an aliquot was checked by TLC. Added the remainder still in portions and continued stirring the slurry. After completion of addition, by TLC, some aldehyde seems to remain so stirring was continued. After another 30 minutes it looked essentially done. Added 400 mL of water and an additional 200 mL of methylene chloride and separated layers. The aqueous phase was made basic with ˜400 mL of 1.0M NaOH and then extracted with 3 times 400 mL of methylene chloride. Concentrated to afford a thick colorless oil. Pumped down to constant weight 28.3 g (67.3%).

Provenance & Evidence