Structure of 191109-49-6
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| CAS No. : | 191109-49-6 |
| Formula : | C12H13NO |
| M.W : | 187.24 |
| SMILES Code : | OC[C@@H](N)C1=CC=C2C=CC=CC2=C1 |
| English Name : | (S)-2-Amino-2-(naphthalen-2-yl)ethan-1-ol |
| MDL No. : | MFCD09253738 |
| InChI Key : | WUEUHTILFFVPQH-GFCCVEGCSA-N |
| Pubchem ID : | 8027553 |
* 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 |
|---|---|---|
| 85% | With tetrabutyl ammonium fluoride In acetonitrile at 60℃; for 7h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogen In ethanol; water Yield given; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 70% | With triethylamine In dichloromethane for 10h; Ambient temperature; | |
| 52% | With triethylamine In dichloromethane at 0℃; for 16h; | |
| 30% | With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With barium dihydroxide; diphenyl phosphoryl azide; triethylamine 1.) toluene, 80 deg C, 8 h, 2.) dioxane, water, reflux, 8 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 40% | With triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere; | N2,N6-bis[(S)-2-hydroxy-1-(naphthalen-2-yl)ethyl]pyridine-2,6-dicarboxamide (9); 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); 1H NMR (500 MHz, CDCl3) δ 8.77 (d, 2H, J = 7.5 Hz), 8.30 (d, 2H, J = 8 Hz), 7.99 (m, 2H), 7.84 - 7.75 (m, 7H), 7.48 - 7.43 (m, 5H), 5.40 (d, 2H, J = 7 Hz), 4.08 (m, 4H); 13C NMR (125 MHz, CDCl3) δ 163.8, 148.8, 139.5, 136.3, 133.5, 133.1, 129.1, 128.1, 127.9, 126.7, 126.4, 125.8, 125.4, 124.8, 66.6, 56.0; HRMS (FAB) calcd for C31H28N3O4 (M+ + H) 506.2080, found 506.2075. |
| In dichloromethane |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 81% | With lithium aluminium tetrahydride In tetrahydrofuran for 18h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: 52 percent / Et3N / CH2Cl2 / 16 h / 0 °C 2: 55 percent / DMAP; triethylmaine; tosyl chloride / CH2Cl2 / 1.5 h / 20 °C | ||
| Multi-step reaction with 3 steps 1: 70 percent / Et3N / CH2Cl2 / 10 h / Ambient temperature 2: SOCl2 / CH2Cl2 / 4 h / Heating 3: 55 percent / NaOH / ethanol; tetrahydrofuran / 1.5 h / Heating | ||
| Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 2: dmap; triethylamine; p-toluenesulfonyl chloride / dichloromethane / 15 h / 20 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 5 steps 1: 82 percent / K2OsO2(OH)4; DABCO; K2CO3 / K3Fe(CN)6 / 2-methyl-propan-2-ol; H2O / 0 °C 2: 65 percent / CH3CN; trifluoromethanesulfonic acid / -40 - 25 °C 3: 66 percent / pyridine / CH2Cl2 / 18.5 h / 0 °C 4: NaOH / methanol / 20 °C 5: 98percent H2SO4 / H2O / Heating | ||
| Multi-step reaction with 2 steps 1: 76 percent / (DHQ)2PHAL, K2OsO2(OH)4, NaOH / propan-1-ol; H2O / 0.42 h / Ambient temperature 2: 85 percent / TBAF / acetonitrile / 7 h / 60 °C | ||
| Multi-step reaction with 4 steps 1: K3Fe(CN)6, K2CO3, (DHQD)2-PHAL, K2OsO4(H2O)2 2: NaOH 3: NaN3, H2O / dimethylformamide 4: LiAlH4 / tetrahydrofuran / Ambient temperature |
| Multi-step reaction with 2 steps 1.1: tert-butylhypochlorite; sodium hydroxide / propan-1-ol / 0.08 h 1.2: 2.33 h / 0 °C 2.1: hydrogenchloride / 1,4-dioxane / 20 °C |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 2: H2O2, LiOH / tetrahydrofuran; H2O / 3 h / Ambient temperature 3: 1.) triethylamine, (PhO)2P(O)N3, 2.) Ba(OH)2*8H2O / 1.) toluene, 80 deg C, 8 h, 2.) dioxane, water, reflux, 8 h |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: H2O2, LiOH / tetrahydrofuran; H2O / 3 h / Ambient temperature 2: 1.) triethylamine, (PhO)2P(O)N3, 2.) Ba(OH)2*8H2O / 1.) toluene, 80 deg C, 8 h, 2.) dioxane, water, reflux, 8 h |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 99% | Stage #1: (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(naphthalen-2-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. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 100% | Stage #1: (1S)-N-(tert-butoxycarbonyl)-1-(2-naphthyl)-2-hydroxyethylamine With hydrogenchloride In 1,4-dioxane at 20℃; Stage #2: With sodium hydrogencarbonate | (1S)-1-(2-Naphthyl)-2-hydroxyethylamine (4); 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. 1H NMR (500 MHz, CDCl3) δ 7.82 (d, 3H, J = 8.5 Hz), 7.77 (s, 1H), 7.49 - 7.42 (m, 3H), 4.21 (br s, 1H), 3.81 (br s, 1H), 2.19 (br s, 3H, OH and NH2); 13C NMR (125 MHz, CDCl3) δ 140.3, 133.6, 133.1, 128.6, 127.9, 127.8, 126.3, 126.2, 125.3, 124.9, 68.2, 57.6; HRMS (EI) calcd for C12H13NO [M+] 187.0997, found 187.0990. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 90% | With triethylamine In dichloromethane at 0 - 20℃; for 18.5h; Inert atmosphere; Schlenk technique; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75% | In dichloromethane at 40℃; for 24h; |

A978720 [2829292-71-7]
(S)-2-Amino-2-(naphthalen-2-yl)ethanol hydrochloride
Reason: Free-Salt