Toluene → 1-Methylethyl((cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

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Reaction Steps

(cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 4) (3.165 g, 9.90 mmol) and DIPEA (5.19 ml, 29.7 mmol) were stirred in dichloromethane (DCM) (66.0 ml) under nitrogen. 1M isopropyl chloroformate in toluene (14.85 ml, 14.85 mmol) was added, the mixture stirred for 2 hours, evaporated to dryness, partitioned between ethyl acetate (200 ml) water (70 ml) and the aqueous layer run off. The organic layer was washed (water (50 ml), brine (20 ml)), dried (sodium sulfate), evaporated to dryness, loaded on to a 40+M Biotage silica column and eluted with cyclohexane:ethyl acetate (9:1 to 1:1). The product containing fractions were evaporated to a white solid (3.23 g). LCMS (Method B): Rt=1.03, MH+=371

Provenance & Evidence