2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID Chemical Properties

Boiling point:

436.7±45.0 °C(Predicted)

Density 

1.222±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.49±0.20(Predicted)

Appearance

White to off-white Solid

2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLIC ACID Usage And Synthesis

Synthesis

To a stirred mixture of (±)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (150 mg, 0.85 mmol) and dichloromethane (1.69 mL) was added di-tert-butyl dicarbonate (185 mg, 0.85 mmol) and triethylamine (177 μL, 1.27 mmol) sequentially at 0 °C. The reaction mixture was gradually warmed to room temperature with continuous stirring overnight. Upon completion of the reaction, the pH was adjusted to 3.0 with 1.0 N aqueous hydrochloric acid, followed by extraction of the reaction mixture with ethyl acetate (3 × 25 mL). The organic phases were combined, washed with saturated aqueous sodium chloride (50 mL), dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to afford 2-N-Boc-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (235 mg, 100% yield). Mass spectral data (m/z): 222 ([M + 2H - t-Bu]+), 300 ([M + Na]+), 577 ([2M + Na]+).

References

[1] Patent: WO2015/94902, 2015, A1. Location in patent: Page/Page column 22
[2] European Journal of Medicinal Chemistry, 2001, vol. 36, # 3, p. 265 - 286
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 314 - 319
[4] Patent: US5391705, 1995, A

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