| Identification | Back Directory | [Name]
(R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL | [CAS]
62855-02-1 | [Synonyms]
H-D-Tic-ol
(R)-1,2,3,4-Tetrahydroisoquinoline-3-methanol
(R)-1,2,3,4-Tetrahydroisoquinolyl-methan-3-ol
(R)-1,2,3,4-tetrahydroisoquinolin-4-ylmethanol
(R)-1,2,3,4-Tetrahydro-3-isoquinolinylmethanol
(3R)-1,2,3,4-tetrahydroisoquinolin-4-ylMethanol
(3R)-1,2,3,4-Tetrahydroisoquinolin-3-ylmethanol
(R)-(+)-1,2,3,4-Tetrahydro-3-isoquinolinemethanol
(R)-(1,2,3,4-tetrahydroisoduinolin-3-yl)-Methanol
3-Isoquinolinemethanol, 1,2,3,4-tetrahydro-, (R)-
(R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL
3-Isoquinolinemethanol, 1,2,3,4-tetrahydro-, (3R)-
3(R)-HYDROXYMETHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
(R)-1,2,3,4-Tetrahydroisoquinolylmethan-3-ol, >=98%
(R)-3-Hydroxymethyl-1, 2, 3, 4-tetrahydroisoquinoline
(R)-1,2,3,4-Tetrahydro-3-isoquinolinylmethanol,99%e.e.
(R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL USP/EP/BP
2-chloro-4-[[2-(diethylamino)-5-methoxyphenyl]methyl]-N,N-dimethylaniline | [Molecular Formula]
C10H13NO | [MDL Number]
MFCD02684327 | [MOL File]
62855-02-1.mol | [Molecular Weight]
163.22 |
| Chemical Properties | Back Directory | [Boiling point ]
307.9±27.0 °C(Predicted) | [density ]
1.081±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Crystalline | [pka]
14.57±0.10(Predicted) | [color ]
White | [Optical Rotation]
101.4°(C=0.01 g/ CHCL3) |
| Hazard Information | Back Directory | [Chemical Properties]
White crystal | [Uses]
(3R)-1,2,3,4-Tetrahydro-3-isoquinolinemethanol is used in asymmetric synthesis of vinylmorpholines by palladium-catalyzed tandem allylic substitutions with amino alcohols. | [Synthesis]
GENERAL STEPS: This experimental procedure was modified with reference to the literature [6]. LiAlH4 (1.98 g, 52.0 mmol) was suspended in anhydrous THF (100 mL) under nitrogen protection, stirred and cooled to 0 °C. Subsequently, a THF solution of methyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (2.50 g, 13.0 mmol) was added slowly and dropwise. The reaction mixture was stirred continuously for 3 h at 0 °C and the progress of the reaction was monitored by thin layer chromatography (TLC) with the unfolding agent being petroleum ether: ethyl acetate (70:30, Rf = 0.43). Upon completion of the reaction, saturated sodium sulfate solution (4 mL) and THF (20 mL) were slowly added to quench the excess LiAlH4 at 0 °C. The inorganic solids were removed by filtration, and the filter cake was washed with ethyl acetate (3 × 30 mL). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford (S)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (4) as a yellow crystalline solid in a yield of 2.09 g (98% yield, melting point 95-97 °C). The spinor data were in agreement with those reported in the 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), 7.01-7.15 (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, 30.9. 47.83, 30.9. | [References]
[1] South African Journal of Chemistry, 2010, vol. 63, p. 195 - 198
[2] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 407 - 414 |
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