Acetic Acid → 1-Methylethyl {(cis)-1-acetyl-2-methyl-6-[2-(1-piperidinylmethyl)-1,3-thiazol-4-yl]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

Beteiligte Stoffe

Reaktionsschritte

1-Methylethyl[(cis)-1-acetyl-6-(2-formyl-1,3-thiazol-4-yl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 39) (21 mg, 0.052 mmol) was dissolved in dichloromethane (DCM) (1 mL), mixed with piperidine (7.77 μL, 0.078 mmol) and acetic acid (7.49 μL, 0.131 mmol) and stirred under nitrogen for 30 minutes. Sodium triacetoxyborohydride (16.63 mg, 0.078 mmol) was added and the mixture was allowed to stir under nitrogen. The mixture was loaded onto a 2 g SCX-column, eluting with MeOH (25 mL) followed by 2M MeOH/NH3 (25 mL). Product-containing fractions were evaporated to dryness to give a solid (18 mg). This was purified on a 12+M Biotage silica column, eluting with 0 to 4% 2N methanolic ammonia in DCM. Product-containing fractions were evaporated to dryness to give a clear, colourless solid (16 mg).

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