Tert-Butylamine → HCID 71290297, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4.10 g (12.9 mmol) of 6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde, 2.83 g (38.7 mmol) of tert-butylamine, 90 g of molecular sieves (4A), and 80 ml of THF was stirred overnight. After decantation of the molecular sieves (they were additionally washed by 2×50 ml of THF), the resulting combined solution was additionally centrifuged to remove slight precipitate. The obtained solution was evaporated to dryness. A solution of the residue in 80 ml of THF was cooled to −80° C., and 50.0 ml (37.5 mmol) of 0.75 M of PhLi in ether was added. The resulting mixture was stirred for 1 h at room temperature. Further on, 20 ml of water was added. The organic layer was separated, and the aqueous layer was extracted with 2×40 ml of ether. The combined organic extract was washed by 20 ml of water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; ethyl acetate-triethylamine=20:1, vol.). Yield 2.84 g (49%) of white solid of a ca. 1 to 1 mixture of two diastereomers. Anal. calc. for C31H37N3: C, 82.44; H, 8.26; N, 9.30. Found: C, 82.59; H, 8.35; N, 9.19. For 1H NMR (in CDCl3) see FIG. 2—Top spectrum.

Provenance & Evidence