7-(benzyloxy)-1,2,3,4-tetrahydroisoquinoline synthesis
- Product Name:7-(benzyloxy)-1,2,3,4-tetrahydroisoquinoline
- CAS Number:252061-94-2
- Molecular formula:C16H17NO
- Molecular Weight:239.31
164148-88-3
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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
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