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[ CAS No. 18881-17-9 ]

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Chemical Structure| 18881-17-9
Chemical Structure| 18881-17-9
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Product Details of [ 18881-17-9 ]

CAS No. :18881-17-9 MDL No. :MFCD01631316
Formula : C10H13NO Boiling Point : 307.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :163.22 g/mol Pubchem ID :776757
Synonyms :

Safety of [ 18881-17-9 ]

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

Application In Synthesis of [ 18881-17-9 ]

  • Upstream synthesis route of [ 18881-17-9 ]
  • Downstream synthetic route of [ 18881-17-9 ]

[ 18881-17-9 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 79815-19-3 ]
  • [ 18881-17-9 ]
YieldReaction ConditionsOperation in experiment
98% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3 h; Inert atmosphere The experimental procedure used for this reaction was adapted from literature.6 To a stirred and cooled suspension of LiAlH4 (1.98 g, 52.0 mmol) in dry THF (100 mL) under aN2 atmosphere, was added dropwise a solution of (S)-methyl1,2,3,4-tetrahydroisoquinoline-3-carboxylate 1 (2.50 g,13.0 mmol) in THF. The mixture was stirred at 0 °C for 3 h, completion of the reaction was monitored by TLC using hexane:ethyl acetate (70:30, Rf = 0.43). Excess LiAlH4 was decomposed by the addition of a saturated sodium sulfate solution (4mL) and THF(20mL)at 0 °C. The inorganic solids were filtered and washed with EtOAc (3 × 30 mL). The combined organic washings were dried (Na2SO4) and removed under reduced pressure to give (S)-3-hydroxymethyl-1, 2, 3, 4-tetrahydroisoquinoline 4 as a crystalline yellow solid: Yield 2.09 g (98percent, mp95–97 °C). Optical rotation as reported in literature.6 1H NMR(400 MHz, CDCl3) δ = 2.57 (dd, 1H, J = 10.8, 11.2 Hz), 2.70 (dd,1H, J = 4.34, 16.42 Hz), 3.05–3.10 (m, 1H), 3.49 (dd, 1H, J = 8.17,10.82 Hz), 3.78 (dd, 1H, J = 3.98, 10.60 Hz), 4.05 (s, 2H) and7.01–7.15 (m, 4H). 13C NMR (100 MHz, CDCl3) δ = 135.6, 133.9,129.3, 126.3, 126.0, 125.9, 65.8, 55.0, 47.83 and 30.9.
65% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3.5 h; Inert atmosphere General procedure: The experimental procedure was adapted from literature. A solution of TIQ ester 4a-e (2.0 g) was added dropwise to a stirred suspension of LiAlH4 (4 mol equiv) in cooled (0 C in ice) dry THF (80 mL) under argon gas flow. The reaction mixture was stirred at 0 C for 1.5 h and then at room temperature for 2 h. The reaction was monitored with TLC (7:3 hexane:ethyl acetate) to confirm the completion of the reaction. After that, THF (20 mL) was added to dilute the reaction mixture and excess LiAlH4 wasdecomposed by the dropwise addition of saturated Na2SO4 at 0 C. The inorganic salts were filtered andwashed with portions of EtOAc (3 x 20 mL). The organic filtrate was dried over MgSO4 andconcentrated in vacuo to give product as a yellow solid.
Reference: [1] South African Journal of Chemistry, 2010, vol. 63, p. 195 - 198
[2] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 407 - 414
  • 2
  • [ 67123-97-1 ]
  • [ 18881-17-9 ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydroxide; boron trifluoride In tetrahydrofuran; methanol Step 1
Synthesis of S-(1,2,3,4-Tetrahydro-Isoquinoline-3-yl)-Methanol STR38
Borane-methyl sulfide complex (31.0 mmol) was added to the gently refluxing solution of S-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid (5.0 g, 28.22 mmol) and boron trifluoride ethorate (28.22 mmol) in THF (100 ML) under nitrogen.
The solution was then refluxed overnight.
The reaction mixture was cooled to 0° C. and quenched by slow addition of methanol (5 ML).
the solvent was evaporated and the residue was dissolved in aqueous solution of sodium hydroxide (6 M) and reflux for 2 hr. the mixture was filtered through a cerite pad.
The filtrate was extracted with chloroform, washed with brine, dried over MgSO4 and evaporated.
The crude product was recrystallized from CHCl3 to give the desired product as crystals (4.0 g, 87percent).
1 H NMR (CDCl3) δ: 7.10 (4 H, m), 4.06 (2H, s), 3.77 (1H, dd, J=10.95 Hz, J=3.64 Hz), 3.52 (1H, dd, J=10.95 Hz, J=7.80 Hz), 3.08 (1H, m), 2.70 (1H, dd, J=16.27 Hz, J=4.26 Hz), 2.59 (1H, dd, J=16.27 Hz, J=10.85 Hz).
13 C NMR (CDCl3) δ: 128.43, 125.34, 125.14, 124.98, 64.81, 54.18, 46.97, 30.05.
Reference: [1] Patent: US6034097, 2000, A,
  • 3
  • [ 74163-81-8 ]
  • [ 18881-17-9 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 20, p. 2883 - 2889
[2] Journal of Organic Chemistry, 1998, vol. 63, # 22, p. 7795 - 7804
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 18, p. 4033 - 4036
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 38, p. 6961 - 6968
[5] Journal of Medicinal Chemistry, 1999, vol. 42, # 11, p. 1982 - 1990
[6] Chemical Communications, 2011, vol. 47, # 38, p. 10746 - 10748
[7] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 407 - 414
  • 4
  • [ 1510832-00-4 ]
  • [ 18881-17-9 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 1, p. 174 - 177
  • 5
  • [ 77497-95-1 ]
  • [ 18881-17-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 12, p. 1335 - 1338
  • 6
  • [ 15912-55-7 ]
  • [ 18881-17-9 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 38, p. 10746 - 10748
  • 7
  • [ 63-91-2 ]
  • [ 18881-17-9 ]
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 407 - 414
[2] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 12, p. 1335 - 1338
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 38, p. 6961 - 6968
  • 8
  • [ 77497-96-2 ]
  • [ 18881-17-9 ]
Reference: [1] Tetrahedron Asymmetry, 1992, vol. 3, # 2, p. 223 - 226
  • 9
  • [ 62708-42-3 ]
  • [ 18881-17-9 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6201 - 6210
  • 10
  • [ 50-00-0 ]
  • [ 63-91-2 ]
  • [ 18881-17-9 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 35, p. 4065 - 4068
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