Acetic Acid → HCID 68640163, compound

Participants

Reaction Steps

A solution of tetrahydrofuran-3-amine (see WO98/08855, 0.500 g, 4.04 mmol) and sodium acetate (0.331 g, 4.04 mmol) in a 1:3 mixture of methanol and tetrahydrofuran (60 ml) was stirred at room temperature. To this was added (tert-butyl-dimethylsilanyloxy)acetaldehyde (2.112 g, 12.12 mmol) followed by glacial acetic acid (1.456 g, 24.24 mmol) and then sodium triacetoxyborohydride (2.568 g, 12.12 mmol) was then added in 5 portions over 3 minutes (CAUTION: vigorous effervescence) and the resulting suspension was left to stir at room temperature for 4 hours. The mixture was evaporated under reduced pressure to leave a thick brown paste which was dissolved in dichloromethane (20 ml) and to this was added a solution of ammonia in methanol (7M solution, 25 ml). The mixture was stirred for 10 minutes and then evaporated under reduced pressure to leave an orange paste which was triturated with dichloromethane (50 ml) and filtered through Celite. The mixture was evaporated under reduced pressure to leave a brown gum which was dissolved in methyl tert-butyl ether (3 ml) and then purified by silica gel chromatography using methyl tert-butyl ether as eluent to give N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)tetrahydrofuran-3-amine (0.446 g, 48% yield) as a brown oil:

Provenance & Evidence