Structure of 1213667-87-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 1213667-87-8 |
| Formula : | C16H27NO |
| M.W : | 249.39 |
| SMILES Code : | OC[C@H](C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1)N |
| English Name : | (S)-2-Amino-2-(3,5-di-tert-butylphenyl)ethanol |
| MDL No. : | MFCD09253894 |
| InChI Key : | GODKSIZLEOJZHJ-CQSZACIVSA-N |
| Pubchem ID : | 66515500 |
* 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 |
|---|---|---|
| 75% | In dichloromethane for 72h; Reflux; | |
| 49% | In tetrahydrofuran at 50℃; for 60h; Inert atmosphere; Sealed tube; | |
| In tetrahydrofuran at 50℃; for 48h; Inert atmosphere; Sealed tube; |
| In dichloromethane Sealed tube; | ||
| In dichloromethane Reflux; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1: hydrogenchloride; methanol / 1,4-dioxane / 1 h / 20 °C 2: dmap; triethylamine / dichloromethane / 4 h / 20 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4: water; potassium hydroxide; methanol / 14 h / 75 °C / Inert atmosphere | ||
| Multi-step reaction with 2 steps 1: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 0 - 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 5 steps 1.1: magnesium / tetrahydrofuran; ethylene dibromide / 1 h / 65 °C / Inert atmosphere; Schlenk technique 1.2: 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.1: titanium(IV) isopropylate / tetrahydrofuran / 12 h / 65 °C / Inert atmosphere 3.1: L-Selectride / tetrahydrofuran / 5 h / -78 °C / Inert atmosphere 4.1: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 0 - 20 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1: titanium(IV) isopropylate / tetrahydrofuran / 12 h / 65 °C / Inert atmosphere 2: L-Selectride / tetrahydrofuran / 5 h / -78 °C / Inert atmosphere 3: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 0 - 20 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: L-Selectride / tetrahydrofuran / 5 h / -78 °C / Inert atmosphere 2: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 0 - 20 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1.98 g | With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 70% | Stage #1: (S)-2-amino-2-(3,5-di-tert-butylphenyl)ethan-1-ol; 2,2-Dimethylmalonyl chloride With triethylamine In dichloromethane at 20℃; for 2h; Stage #2: With dmap; triethylamine; p-toluenesulfonyl chloride In dichloromethane at 20℃; for 48h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogenchloride In 1,4-dioxane; methanol; water at 20℃; for 16h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With triethylamine In dichloromethane at 0 - 20℃; for 12.5h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With triethylamine In dichloromethane at 0 - 20℃; for 1.5h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h; Schlenk technique; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 16 h / 20 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine; methanesulfonyl chloride / dichloromethane / 16 h / 50 °C / Schlenk technique; Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 0.24 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: (S)-2-amino-2-(3,5-di-tert-butylphenyl)ethan-1-ol In N,N-dimethyl-formamide at 20℃; for 36h; Stage #3: With triethylamine; p-toluenesulfonyl chloride In dichloromethane at 20 - 40℃; for 4.5h; | 12.2 (2) Synthesis of (S)-4-(3,5-di-tert-butylphenyl)-2-[1-(2-pyridyl)-1H-indol-2-yl]-4,5-dihydro-1,3-oxazole (structural formula L12): The carboxylic acid product with structural formula d (0.40 g, 1.70 mmol) was added sequentially to a reactor along with the condensing agent N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)hexafluorophosphate urea. (HATU) (1.93 g, 5.04 mmol) was added to 10 mL of N,N-dimethylformamide (DMF), followed by dropwise addition of triethylamine (TEA) (1.87 mL, 13.44 mmol). After reacting at room temperature for 1 hour, (S)-2-amino-2-(3,5-bis(tert-butyl)phenyl)ethanol (0.63 g, 2.50 mmol) with structural formula 12e was added, and the reaction was carried out at room temperature for 36 hours. 10 mL of water was added, followed by extraction 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. The specific conditions were: the column was packed with petroleum ether, and the eluent was petroleum ether:ethyl acetate at a ratio of 1:2, yielding a brown viscous liquid (0.43 g, 55% yield). The amide product with structural formula 12f (0.43 g, 0.92 mmol), p-toluenesulfonyl chloride (TsCl) (0.53 g, 2.75 mmol), 10 mL of dichloromethane, and triethylamine (TEA) (0.37 mL, 2.53 mmol) were added sequentially to a reactor. The reaction was carried out at room temperature for 30 minutes, followed by the dropwise addition of triethylamine (TEA) (1.54 mL, 11.21 mmol). A reflux condenser was attached, and the heating plate temperature was adjusted to 40 °C. Heating was stopped after 4 hours. The mixture was cooled to room temperature, 10 mL of water was added, and the mixture was then extracted three times with dichloromethane (10 mL). The extract was dried, concentrated, and subjected to column chromatography. The specific conditions were: the column was packed with petroleum ether, and the eluent was petroleum ether:ethyl acetate at a ratio of 3:1, yielding an orange-red viscous liquid (0.24 g, 58% yield). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 92% | With toluene-4-sulfonic acid In toluene at 80℃; for 20h; |