Formaldehyde → 1,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acid

関与物質

反応条件

反応手順

To a suspension of DL-m-tyrosine (5.00 g, 11.0 mmol) in 0.05 N HCl (50 mL) was added 37% aq. formaldehyde (5.00 mL, 5.2 g, 64.0 mmol) and the resulting slurry was heated at 90° C. for 1 h and then cooled to RT. The mixture was filtered and the resulting solid was washed with H2O and acetone and dried in vacuo to yield 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (3.31 g, 52% yield) as an off-white solid. MS (EI) m/z: 194.0 (M+H+). 1H NMR (400 MHz, CD3OD): δ 7.03 (d, J=8.0 Hz, 1H), 6.69 (dd, J=8.8, and 2.4 Hz, 1H), 7.00 (s, 1H), 4.28-4.19 (m, 2H), 3.80 (dd, J=11.6, and 5.2 Hz, 1H), 3.31-3.27 (m, 1H), 3.05 (dd, J=16.8, and 11.2 Hz, 1H), acid, hydroxy and amine protons not visible.

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