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[ CAS No. 63905-73-7 ] {[proInfo.proName]}

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Chemical Structure| 63905-73-7
Chemical Structure| 63905-73-7
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Product Details of [ 63905-73-7 ]

CAS No. :63905-73-7 MDL No. :MFCD01444791
Formula : C9H12ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 185.65 Pubchem ID :-
Synonyms :

Safety of [ 63905-73-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 63905-73-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 63905-73-7 ]
  • Downstream synthetic route of [ 63905-73-7 ]

[ 63905-73-7 ] Synthesis Path-Upstream   1~3

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  • [ 63905-73-7 ]
  • [ 14446-24-3 ]
Reference: [1] Patent: WO2009/105715, 2009, A1, . Location in patent: Page/Page column 24-25
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  • [ 24424-99-5 ]
  • [ 63905-73-7 ]
  • [ 158984-83-9 ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine In methanol; ethyl acetate Referential Example 139
2-tert-Butoxycarbonyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline
In methanol (100 ml), 6-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (7.87 g) was dissolved, followed by the addition of triethylamine (4.67 ml) and di-tert-butyl dicarbonate (13.95 g).
The resulting mixture was stirred at room temperature for 3 hours.
To the residue obtained by concentrating the reaction mixture under reduced pressure, ethyl acetate was added.
The resulting mixture was washed with 1N hydrochloric acid and dried over anhydrous sodium sulfate.
The solvent was then distilled off under reduced pressure.
The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=10:1~3:1), whereby the title compound (9.96 g, 94percent) was obtained.
1H-NMR (CDCl3) δ: 1.49(9H,s), 2.75(2H,t,J=5.9 Hz), 3.61(2H,t,J=5.9 Hz), 4.48(2H,s), 6.25(1H,br s), 6.64(1H,d,J=2.4 Hz), 6.70(1H,br s), 6.93(1H,d,J=7.8 Hz).
65% With sodium hydrogencarbonate In chloroform; water at 20℃; Example 291: 6-hydroxy-3,4-dihydro-lH-isoquinoline-2-carboxylic acid toerf-butyl ester A solution of l,2,3,4-tetrahydro-isoquinolin-6-ol, HCl salt (2 g, 10 mmol) and di-tert- butyldicarbonate (4 g, 18 mmol) in saturated aqueous sodium bicarbonate solution (20 mL) and chloroform (20 mL) was stirred at room temperature overnight. The organic phase was washed with water, dried over MgSO4, filtered and concentrated. The crude was purified via a silica gel column eluted with EtOAc in hexanes from 0 to 100percent to give desired product (1.7 g, yield: 65percent).
0.58 g With sodium hydrogencarbonate In chloroform; water at 20℃; A solution of 1,2,3, 4-tetrahydroisoquinolin-6-ol HCl (1 g, 5.39 mmol) and BOC20 (2.251 ml, 9.70 mmol) in saturated aqueous sodium bicarbonate solution (10 mL) and chloroform (10 mL) was stirred at room temperature overnight. The aqueous portion was neutralized with concentrated HCl and extracted with ethyl acetate. The combined organic portions were washed with 0.1 N HCl, dried over MgS04, filtered and concentrated to give 1.6 g of a yellow oil. The oil was chromatographed on silica gel with 0-60percent ethyl acetate in hexanes to provide 0.58 g of product. 1H NMR (400MHz, CHLOROFORM-d) δ 6.99 (d, J=8.3 Hz, IH), 6.70 (dd, J=8.3, 2.5 Hz, IH), 6.64 (d, J=2.5 Hz, IH), 4.52 (s, 2H), 3.64 (t, J=5.9 Hz, 2H), 2.80 (t, J=5.9 Hz, 2H), 1.62-1.46 (m, 13H).
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5167 - 5182
[2] Patent: US6525042, 2003, B1,
[3] Patent: WO2011/17561, 2011, A1, . Location in patent: Page/Page column 147-148
[4] Patent: WO2015/34820, 2015, A1, . Location in patent: Page/Page column 44
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Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5167 - 5182
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