Trimethyl orthoformate → HCID 59129101, compound

Participants

Reaction Steps

A mixture of 2,3,4,5-tetrahydro-1H-benzo[d]azepin-6-ol (see Demarinis et al. J. Med. Chem. 1984, 27, 918-921) (60 mg, 0.37 mmol), trimethylacetaldehyde (400 μL, 3.7 mmol), trimethyl orthoformate (390 μL, 3.7 mmol) and glacial acetic acid (40 μL) in 1-methyl-2-pyrrolidinone (2.5 mL) was stirred at rt for 2.5 h. Sodium triacetoxyborohydride (388 mg, 1.8 mmol) was then added and the mixture was stirred at room temperature for 16 h. The mixture was then loaded on top of a silica gel-SCX (sulfonic acid) column and eluted first with methanol, then with 2 M ammonia in methanol. The latter fraction was evaporated and the resulting 3-neopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-6-ol was used in the next step without further purification. (M+H)+=234.0.

Provenance & Evidence