Structure of 39110-76-4
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CAS No. : | 39110-76-4 |
Formula : | C14H28O2 |
M.W : | 207.70 |
SMILES Code : | CC(N)C1=CC=C2C=CC=CC2=C1.[H]Cl |
MDL No. : | MFCD09971448 |
InChI Key : | SVJSCAQZYGXVIL-UHFFFAOYSA-N |
Pubchem ID : | 24686261 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; water; under 760.051 Torr; | First step, hydroxyamine hydrochloride (4.1 g) and NaOAc (9.6 g) were added to a solution of 2-acetonaphthone (5 g) in EtOH (80 ml). The reaction mixture was stirred at 60C for 6 h. EtOH was removed under reduced pressure. H2O (40 ml) was added to the residue, and the resulting solution was extracted with EtOAc (3 × 40 ml). The EtOAc of the combined organic layer was removed by rotary evaporation under reduced pressure to yield 2-acetonaphthone oxime (5.45 g) as a pale yellowish solid. Second step, 2-acetonaphthone oxime (5.45g) and concentrated HCl (15.53 ml) in EtOH (50 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (623 mg). The reaction solution was filtered and the filtrate was concentrated. The residue was suspended in EtOAc, and the suspension was filtered to yield 1-(naphthalene-2-yl)-ethylamine hydrochloride (6.0 g) as a white solid. Third step, a mixture of 1-(naphthalene-2-yl)-ethylamine (436 mg, the hydrochloride), 6-chloropurine riboside (200 mg) and triethylamine (3 ml) in PrOH (60ml) was heated to 70C and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (20 : 1) to yield N6-[(+/-)-1-(naphthalene-2-yl)-ethyl]-adenosine(240 mg) as a white solid: positive ESIMS m/z 422 [M + H]+, 444 [M + Na]+ and 460[M+K]+; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety δ 8.43 (1H, m, -NH), 8.41 (1H, m, H-2), 8.19 (1H, s, H-8), 5.91 (1H, d, J= 6.0 Hz, H-1'), 5.46 (2H, m, 2×-OH), 5.23 (1H, d, J = 4.2 Hz, -OH), 4.63 (1H, m, H-2'), 4.17 (1H, m, H-3'), 4.00 (1H, m, H-4'), 3.69 (1H, m, H-5'a), 3.56 (1H, m, H-5'b); the (+/-)-1-(naphthalene-2-yl)-ethyl moiety δ 7.90 (1H, brs, H-1), 7.84 (3H, m, H-4", H-5", H-8"), 7.64 (1H, d, J= 8.4 Hz, H-3"), 7.43 (2H, m, H-6", H-7"), 5.68 (1H, m, H-9"), 1.63 (3H, d, J = 7.2 Hz, H-10"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety δ 154.0 (s, C-6), 152.4 (d, C-2), 148.7 (s, C-4), 139.9 (d, C-8), 119.9 (s, C-5), 88.1 (d, C-1), 86.0 (d, C-4'), 73.6 (d, C-2'), 70.7 (d, C-3'), 61.7 (d, C-5'); the (+/-)-1-(naphthalene-2-yl)-ethyl moiety δ 142.8 (s, C-2"), 132.9 (s, C-4"a), 132.1 (s, C-8"a), 127.9 (d, C-4"), 127.7 (s, C-7"), 127.5 (d, C-6"), 126.2 (d, C-5"), 125.6 (d, C-8"), 125.2 (d, C-3"), 124.2 (d, C-1), 49.1 (d, C-9"), 22.5 (q, C-10)ο | |
6.0 g | With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr; | Second step, 2-acetonaphthone oxime (5.45 g) and concentrated HCl (15.53 ml) in EtOH (50 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (623 mg). The reaction solution was filtered and the filtrate was concentrated. The residue was suspended in EtOAc, and the suspension was filtered to yield 1-(naphthalene-2-yl)-ethylamine hydrochloride (6.0 g) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
240 mg | With triethylamine; In propan-1-ol; at 70℃; for 8h; | Third step, a mixture of 1-(naphthalene-2-yl)-ethylamine (436 mg, the hydrochloride), 6-chloropurine riboside (200 mg) and triethylamine (3 ml) in PrOH (60 ml) was heated to 70 C. and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (20:1) to yield N6-[(+/-)-1-(naphthalene-2-yl)-ethyl]-adenosine (240 mg) as a white solid: positive ESIMS m/z 422 [M+H]+, 444 [M+Na]+ and 460[M+K]+; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety δ 8.43 (1H, m, -NH), 8.41 (1H, m, H-2), 8.19 (1H, s, H-8), 5.91 (1H, d, J=6.0 Hz, H-1'), 5.46 (2H, m, 2*-OH), 5.23 (1H, d, J=4.2 Hz, -OH), 4.63 (1H, m, H-2'), 4.17 (1H, m, H-3'), 4.00 (1H, m, H-4'), 3.69 (1H, m, H-5'a), 3.56 (1H, m, H-5'b); the (+-)-1-(naphthalene-2-yl)-ethyl moiety δ 7.90 (1H, brs, H-1"), 7.84 (3H, m, H-4", H-5", H-8"), 7.64 (1H, d, J=8.4 Hz, H-3"), 7.43 (2H, m, H-6", H-7"), 5.68 (1H, m, H-9"), 1.63 (3H, d, J=7.2 Hz, H-10"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety δ 154.0 (s, C-6), 152.4 (d, C-2), 148.7 (s, C-4), 139.9 (d, C-8), 119.9 (s, C-5), 88.1 (d, C-1'), 86.0 (d, C-4'), 73.6 (d, C-2'), 70.7 (d, C-3'), 61.7 (d, C-5'); the (+/-)-1-(naphthalene-2-yl)-ethyl moiety δ 142.8 (s, C-2"), 132.9 (s, C-4"a), 132.1 (s, C-8"a), 127.9 (d, C-4"), 127.7 (s, C-7"), 127.5 (d, C-6"), 126.2 (d, C-5"), 125.6 (d, C-8"), 125.2 (d, C-3"), 124.2 (d, C-1"), 49.1 (d, C-9"), 22.5 (q, C-10"). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The 1,1,3-triphenyl-2-methylacetylene-1-alcohol (152 mg, 1.0 mmol), cat. [Au] (6 mg, 1 µM %), AgOTf (2.6 mg, 1 µM %), water (36 mg, 2 mmol) and methanol (1 ml) are added to the 25 mL of Claisen tube or. After closing the reaction at 120 C for 6 hours, cooling to room temperature. Then adding formic acid amine (315 mg, 5 mmol) and cat. [Rh] (6.2 mg, 1 mmol %), the reaction mixture in oil bath heated to 80 C, reaction 12 hours, cooling to room temperature. Rotary evaporation of the solvent and add a certain amount of ethyl acetate and water extraction, the organic phase of the resulting product after concentrated hydrochloric acid the reflux process, rotary evaporation to remove the solvent, the final petroleum ether washing and filtering to obtain the pure target compound, yield: 84% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,6-bis(3,5-bis(3,7-bis(trifluoromethyl)naphthalen-1-yl)phenyl)-4H-dinaphtho[2,1-d:1',2'-f][1,3,2]dithiazepine 3,3,5,5-tetraoxide; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate; In tert-butyl methyl ether; methyl cyclohexane; at 20℃; for 24h;Inert atmosphere; Molecular sieve; | General procedure: An oven-dried 10 mL vial was charged with hydrochloride salt of imine 1 (0.25 mmol),Hantzsch ester 2 (108.3 mg, 0.35 mmol, 1.4 equiv.), disulfonimide DSI-3c, freshly activatedmolecular sieve 5Å (250 mg) and a magnetic stirring bar at RT. Then 7.5 mL (0.033 M) ofMTBE:MeCy (in the case of 1l used MTBE:CHCl3) was added under argon atmosphere.The mixture was then introduced to the desired temperature for the reaction. The reactionmixture was filtered over Celite, washed with iso-hexane (40 mL), and iso-hexane:MTBE(1:1, 40 mL) to remove the neutral compounds, followed by the hydrochloride salt of amineproduct was collected by washing with 3% MeOH in CH2Cl2 (60 mL) and the filtrate wasevaporated under reduced pressure to afford the desired hydrochloride salt of amine products4 in >99% purity (by 1H NMR). The hydrochloride salt of amine product 4 (0.01 mmol) wasbenzoylated following a standard procedure to determine the enantiomeric ratio by HPLC.To determine the crude reaction enantiomeric ratio, following the general procedure usinghydrochloride salt of imine 1 (0.03 mmol scale), the reaction was quenched with sat.NaHCO3 solution and the amine product was extracted with MTBE and benzoylatedfollowing a standard procedure. |
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