Acetic Acid → HCID 86669248, compound

Participants

Reaction Steps

1-Methylethyl[(cis)-1-acetyl-6-(5-formyl-2-furanyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 21) (18 mg, 0.047 mmol) was dissolved in dichloromethane (DCM) (1 mL), mixed with acetic acid (8.04 μL, 0.140 mmol) and piperidine (9.27 μL, 0.094 mmol) and stirred under nitrogen for 30 minutes. sodium triacetoxyborohydride (12.90 mg, 0.061 mmol) was added and the reaction was stirred again under nitrogen. After 17 hours reaction time a second quantity of sodium triacetoxyborohydride (12.90 mg, 0.061 mmol) was added. 1 hour after this another sample of sodium triacetoxyborohydride (12.90 mg, 0.061 mmol) was added. After 2 further hours the reaction was loaded onto a 2 g Flash SCX-column, eluting with MeOH (60 mL) followed by 2M MeOH/NH3 (60 mL). The product-containing fraction was evaporated to dryness to give a brown solid which was purified by MDAP. Product-containing fractions were evaporated to dryness to give a clear, colourless solid (3 mg).

Provenance & Evidence