ChemicalBook CAS DataBase List 7-(benzyloxy)-1,2,3,4-tetrahydroisoquinoline

7-(benzyloxy)-1,2,3,4-tetrahydroisoquinoline synthesis

12synthesis methods

Product Name:7-(benzyloxy)-1,2,3,4-tetrahydroisoquinoline
CAS Number:252061-94-2
Molecular formula:C16H17NO
Molecular Weight:239.31

2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-6-(phenylmethoxy)-, 1,1-dimethylethyl ester

164148-88-3
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7-(benzyloxy)-1,2,3,4-tetrahydroisoquinoline

252061-94-2
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Yield:252061-94-2 99.3%

Reaction Conditions:

with trifluoroacetic acid in dichloromethane at 20; for 12 h;

Steps:

9-15 tert-butyl 6-benzyloxy-3,4-dihydro-1H-isoquinoline-2-carboxylate.

To a solution of tert-butyl 6-benzyloxy-3,4-dihydro-1H-isoquinoline-2-carboxylate (200 mg, 0.589 mmol) in DCM (5 mL) was added TFA (0.5 mL, 6.49 mmol).
The mixture was stirred at 20° C. for 12 hours.
The resulting mixture was quenched by addition of saturated NaHCO₃ aqueous solution (10 mL) and extracted with DCM (20 mL*3).
The combined organic layer was dried over anhydrous Na₂SO₄, filtered and concentrated under reduced pressure to afford 6-benzyloxy-1,2,3,4-tetrahydroisoquinoline (140 mg, 99.3% yield) as yellow gum. ¹H NMR (400 MHz, methanol-d₄) δ ppm 7.39-7.44 (m, 2H), 7.33-7.38 (m, 2H), 7.26-7.32 (m, 1H), 6.95 (d, J=8.4 Hz, 1H), 6.76-6.80 (m, 1H), 6.74 (d, J=2.4 Hz, 1H), 5.04 (s, 2H), 3.91 (s, 2H), 3.04-3.10 (m, 2H), 2.81 (t, J=6.0 Hz, 2H).

References:

US11077101,2021,B1 Location in patent:Page/Page column 1065-1068

50-00-0 Synthesis