6-BROMO-3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

374.2±42.0 °C(Predicted)

Density 

1.353±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-1.56±0.20(Predicted)

Appearance

Colorless to light yellow Solid-Liquid Mixture

InChI

InChI=1S/C14H18BrNO2/c1-14(2,3)18-13(17)16-7-6-10-8-12(15)5-4-11(10)9-16/h4-5,8H,6-7,9H2,1-3H3

InChIKey

SZIPGDGOBMFCEH-UHFFFAOYSA-N

SMILES

C1C2=C(C=C(Br)C=C2)CCN1C(OC(C)(C)C)=O

6-BROMO-3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

Di-tert-butyl dicarbonate (3.52 g, 16.14 mmol) was slowly added to a solution of 6-bromo-1,2,3,4-tetrahydroisoquinoline (3.26 g, 15.37 mmol) in tetrahydrofuran (45 mL) at room temperature. The reaction mixture was stirred continuously for 15 h at room temperature. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using solvent gradient elution (0→8% ethyl acetate/hexane) to afford the target compound tert-butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (5.05 g, 16.18 mmol, quantitative yield) as a colorless oil.1H NMR (300 MHz, CDCl3) δ: 1.49 (9H, s) ), 2.80 (2H, t, J = 5.9 Hz), 3.62 (2H, t, J = 5.9 Hz), 4.51 (2H, s), 6.97 (1H, d, J = 8.7 Hz), 7.28-7.32 (2H, m).

References

[1] Patent: EP3192791, 2017, A1. Location in patent: Paragraph 0594
[2] ChemMedChem, 2018, vol. 13, # 14, p. 1405 - 1413
[3] Patent: WO2013/80222, 2013, A1. Location in patent: Page/Page column 40
[4] Patent: WO2017/184662, 2017, A1. Location in patent: Page/Page column 58
[5] Patent: WO2017/68412, 2017, A1. Location in patent: Page/Page column 274

6-BROMO-3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLIC ACID TERT-BUTYL ESTER(893566-74-0)Related Product Information

• 1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE
• TERT-BUTYL 8-BROMO-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE
• 2-(TERT-BUTOXYCARBONYL)-1,2,3,4-TETRAHYDROISOQUINOLINE-6-CARBOXYLIC ACID
• TERT-BUTYL 6-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE
• TERT-BUTYL 8-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE
• TERT-BUTYL 5-HYDROXY-3,4-DIHYDROQUINOLINE-1(2H)-CARBOXYLATE
• 5-BROMO-3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLIC ACID TERT-BUTYL ESTER
• 3,4-DIHYDROISOQUINOLINE
• 6-BROMO-3,4-DIHYDRO-1H-ISOQUINOLINE-2-CARBOXYLIC ACID TERT-BUTYL ESTER
• (4-BROMO-BENZYL)-METHYL-CARBAMIC ACID TERT-BUTYL ESTER
• 6-bromo-1,2,3,4-tetrahydroisoquinoline
• 2-BOC-6-BROMO-3,4-DIHYDRO-1H-ISOQUINOLINE-1-CARBOXYLIC ACID