Structure of 1091606-67-5
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CAS No. : | 1091606-67-5 |
Formula : | C26H24NP |
M.W : | 381.44 |
SMILES Code : | N[C@@H](C1=CC=CC=C1)[C@@H](P(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4 |
MDL No. : | MFCD11045444 |
InChI Key : | MIPGTOGPLXZBQX-UIOOFZCWSA-N |
Pubchem ID : | 46177587 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-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 |
---|---|---|
Tetrahydrofuran (20 ml) was added to a mixture of the S-binap ligand (0.5 g, 0.8 mmol) and [RuCl2(benzene)]2 (200 mg, 0.4 mmol), followed by DMF (0.5 ml) and the mixture refluxed for 6 hours under argon. The solvent was removed under reduced pressure and a solution of the aminophosphine (0.8 mmol) in toluene 20 added. The mixture was refluxed for 4 hours and the solvent removed under reduced pressure. Ether (10 ml) was then added and the mixture stirred for 2 hours under argon. The solids were filtered, washed with ether and dried under vacuum. The catalysts were |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With tetrafluoroboric acid; In dichloromethane; water; at 20℃; for 0.5h;Inert atmosphere; | To a solution of <strong>[1091606-67-5](1S,2S)-2-(Diphenylphosphino)1,2-diphenylethylammine</strong> (0.091 g, 0.24 mmol) in CH2Cl2 (5 mL) was added an aqueous solution of HBF4 (0.033 mL, 48 wt %) dropwise via syringe. After stirring for 30 minutes at ambient temperature the organic layer was removed, dried over MgSO4, and then reduced to dryness leaving a white solid (1g). The solid was redissolved in CH2Cl2 (1 mL) and then hexanes was added to afford a white solid which was filtered off and dried in vacuo. Yield 0.067 g (60%). 1H NMR (300 MHz, CD2Cl2): d 4.48 (1br, 1H, CH), 4.68 (1br, 1H, CH), 6.50-7.92 (br m, 20H, Ar). 31P NMR (121.4 MHz, CD2Cl2): d -9.95 (s). 19F NMR (282.3 MHz, CD2Cl2): d -148.0(s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |
A731185 [1091606-68-6]
(1R,2R)-2-(Diphenylphosphino)-1,2-diphenylethanamine
Reason: