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Chemical Structure| 110480-82-5 Chemical Structure| 110480-82-5

Structure of 110480-82-5

Chemical Structure| 110480-82-5

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Product Details of [ 110480-82-5 ]

CAS No. :110480-82-5
Formula : C12H13NO
M.W : 187.24
SMILES Code : OC[C@@H](N)C1=C2C=CC=CC2=CC=C1
English Name :(S)-2-Amino-2-(naphthalen-1-yl)ethan-1-ol
MDL No. :MFCD09253738

Safety of [ 110480-82-5 ]

Application In Synthesis of [ 110480-82-5 ]

* 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.

  • Downstream synthetic route of [ 110480-82-5 ]

[ 110480-82-5 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 5659-93-8 ]
  • [ 110480-82-5 ]
  • [ 529489-02-9 ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine In dichloromethane at 0℃; for 1.5h;
37% With triethylamine at -20℃; Inert atmosphere;
  • 2
  • [ 1312719-19-9 ]
  • [ 110480-82-5 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(naphthalen-1-yl)ethyl)-2-methylpropane-2-sulfinamide With hydrogenchloride In methanol at 20℃; for 3h; Stage #2: With sodium hydrogencarbonate In water 4.6.1. (S)-2-Amino-2-(4-fluorophenyl)ethanol 1a General procedure: At first, (Rs,2S)-N-((tert-butyldimethylsilyloxy)-1-(4-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide 8a (0.280 g, 0.749 mmol) was dissolved in MeOH (10 mL) and then HCl/MeOH (4 M, 2.0 mL) was added. The mixture was stirred at room temperature for 3 h. The solvent was removed under vacuum and the residue neutralized with saturated NaHCO3 (20 mL). The mixture was extracted with CH2Cl2/MeOH (10:1, 3 × 50 mL) and the organic phases dried (Na2SO4) and concentrated to give 0.11 g (93%) of (S)-2-amino-2-(4-fluorophenyl)ethanol as a white solid.
  • 3
  • [ 3739-94-4 ]
  • [ 110480-82-5 ]
  • [ 1393524-53-2 ]
YieldReaction ConditionsOperation in experiment
64% With triethylamine In dichloromethane at -10℃; for 0.416667h; Inert atmosphere; N2,N6-bis[(S)-2-hydroxy-1-(naphthalen-2-yl)ethyl]pyridine-2,6-dicarboxamide (9); General procedure: A solution of 2,6-pyridine-dicarbonyldichloride (152 mg, 0.745 mmol, 1 equiv) in 3.5 mL CH2Cl2 was added to a 100-mL round-bottom flask charged with (1S)-1-(2-naphthyl)-2-hydroxyethylamine (279 mg, 1.49 mmol, 2 equiv) in 14 mL of CH2Cl2 and Et3N (0.54 mL, 3.88 mmol, 5.2 equiv) at 0 °C under N2. The reaction mixture was a clear dark yellow solution, which was stirred for 1 h, and the reaction was complete with the disappearance of the starting material. Workup employed 10 mL CH2Cl2 followed by 36 mL saturated NaHCO3. The aqueous layer was extracted with CH2Cl2, and combined organic layers were washed with brine. The combined organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Flash column chromatography gave a yellow solid product (0.15 g, 40%) with Rf= 0.68 (85% EtOAc/hexanes);
  • 4
  • [ 1393524-52-1 ]
  • [ 110480-82-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (1S)-N-(tert-butoxycarbonyl)-1-(1-naphthyl)-2-hydroxyethylamine With hydrogenchloride In 1,4-dioxane at 20℃; Stage #2: With sodium hydrogencarbonate (1S)-1-(2-Naphthyl)-2-hydroxyethylamine (4); General procedure: The white starting material 2 (0.1 g, 0.35 mmol, 1 equiv) was dissolved upon stirring in 2 mL of 4 M HCl in dioxane at room temperature, giving a clear light yellow solution. After 1 min, a light brownish yellow precipitate formed. The reaction mixture was allowed to stir until no starting material spot was observed on TLC. The reaction mixture was concentrated in vacuo to afford a pale-yellow solid, which was washed with saturated NaHCO3, and extracted with CH2Cl2. The combined extracts were dried over Na2SO4. The dried solution was filtered and concentrated, giving a pale yellow solid crude product, which has no need for further purification.
  • 5
  • [ 7321-55-3 ]
  • [ 110480-82-5 ]
  • [ 245093-03-2 ]
YieldReaction ConditionsOperation in experiment
61% With zinc(II) chloride In chlorobenzene for 48h; Inert atmosphere; Reflux; 2,2-Bis{2-[4(S)-1-naphthyl-1,3- (8); A solution of the corresponding naphthylamino alcohol (0.14 g, 0.76 mmol, 2 equiv) in PhCl was added to a flame-dried 50-mL 2-neck round-bottom flask charged with heat-fused ZnCl2 (0.31 g, 2.3 mmol, 6 equiv), and dimethylmalononitrile (0.036 g, 0.38 mmol, 1 equiv). The reaction mixture was then heated to reflux for 48 h. The resulting yellow solution was cooled to rt, and 12 mL of saturated NH4Cl was added with vigorous stirring, rendering the mixture homogeneous. The organic layer was collected, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography with 10% to 30% EtOAc/hexanes. The light yellow solid product (0.101 g, 61%) obtained was not very stable at room temperature (decomposition was observed, and the resulting mixture was purified once again by column chromatography to afford 82 mg of product). 13C NMR (125 MHz, CDCl3) δ 170.8, 139.9, 138.6, 134.1, 129.1, 128.1, 126.5, 126.0, 124.8, 123.7, 122.9, 75.6, 69.9, 39.5, 24.8.
  • 6
  • [ 110470-39-8 ]
  • [ 110480-82-5 ]
YieldReaction ConditionsOperation in experiment
83% With sodium tetrahydroborate In methanol at 0 - 20℃; for 24h;
  • 7
  • [ CAS Unavailable ]
  • [ 110480-82-5 ]
  • [ 3113596-61-2 ]
YieldReaction ConditionsOperation in experiment
0.25 g Stage #1: carboxylic acid 1-(pyridin-2-yl)-1H-indole-2-carboxylic acid With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-(S)-amino-2-(naphthalen-1-yl)ethanol In N,N-dimethyl-formamide at 20℃; for 36h; Stage #3: With triethylamine; p-toluenesulfonyl chloride In dichloromethane at 20 - 40℃; for 4.5h; 13.2 (2) Synthesis of (S)-4-(1-naphthyl)-2-[1-(2-pyridyl)-1H-indol-2-yl]-4,5-dihydro-1,3-oxazole (Structural Formula L13): The carboxylic acid product with structural formula d (0.40 g, 1.70 mmol), the condensing agent N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)hexafluorophosphate urea (HATU) (1.94 g, 5.16 mmol), and N,N-dimethylformamide (DMF) 10 mL were added sequentially to a reactor. Then, triethylamine (TEA) (1.94 mL, 13.81 mmol) was added dropwise. After reacting at room temperature for 1 hour, (S)-2-amino-2-(naphthyl-1-yl)ethanol with structural formula 13e (0.48 g, 2.55 mmol) was added, and the reaction was carried out at room temperature for 36 hours. Add 10 mL of water, then extract three times with ethyl acetate (10 mL). The extracted organic phase was then washed three times with water (10 mL) to remove DMF, dried, concentrated, and subjected to column chromatography. Specific conditions were: a column packed with petroleum ether, with a petroleum ether:ethyl acetate ratio of 1:1 as the eluent, yielding a brown viscous liquid (0.59 g, 84% yield). In a reactor, the amide product with structural formula 13f (0.59 g, 1.43 mmol), p-toluenesulfonyl chloride (TsCl) (0.84 g, 4.29 mmol), 5 mL of dichloromethane, and triethylamine (TEA) (0.57 mL, 3.94 mmol) were added sequentially. The reaction was carried out at room temperature for 30 minutes, followed by dropwise addition of triethylamine (TEA) (2.40 mL, 17.47 mmol). A reflux condenser was attached, and the heating plate temperature was adjusted to 40 °C. Heating was stopped after 4 hours of reaction. Cool to room temperature, add 5 mL of water, then extract three times with dichloromethane (5 mL), followed by drying, concentration, and column chromatography. Specific conditions: column packed with petroleum ether, eluent of petroleum ether:ethyl acetate at a ratio of 4:1, yielding a powdery white viscous liquid (0.25 g, 44% yield).
 

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