* 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.
With L-Tartaric acid In isopropyl alcohol for 2 h;
3-Phenylpiperidine (1,100 g, 621.1 mmol) was dissolved in isopropanol (50 mL).Will be dissolved in L-tartaric acid (93.16g, 622.2mmol)Isopropyl alcohol (200mL)The solution was added dropwise to a solution of racemic 3-phenylpiperidine in isopropanol and stirred for 2 h.Filtration to obtain tartrate;Then, methanol (10 L) was added to the tartrate, and after heating to complete dissolution, the stirring was stopped; the temperature was slowly lowered to room temperature, and the mixture was crystallized at -20 ° C for 7 days, and filtered to obtain a crude white solid.A 1N aqueous sodium hydroxide solution (50 mL) was added, and ethyl acetate (25 mL×2)The combined organic layers were dried with anhydrous sodium sulfate, filtered and evaporated.
Reference：
[1] Patent: CN108203404, 2018, A, . Location in patent: Paragraph 0123-0142
2
[ 3973-62-4 ]
[ 59349-71-2 ]
[ 430461-56-6 ]
Yield
Reaction Conditions
Operation in experiment
89.19 % ee
With (R)-10-camphorsulfonic acid In ethanol for 2 h;
3-Phenylpiperidine (1,100 g, 621.1 mmol) was dissolved in isopropanol (50 mL).Will be dissolved in L-tartaric acid (93.16g, 622.2mmol)Isopropyl alcohol (200mL)The solution was added dropwise to a solution of racemic 3-phenylpiperidine in isopropanol and stirred for 2 h.Filtration to obtain tartrate;Then, methanol (10 L) was added to the tartrate, and after heating to complete dissolution, the stirring was stopped; the temperature was slowly lowered to room temperature, and the mixture was crystallized at -20 ° C for 7 days, and filtered to obtain a crude white solid.A 1N aqueous sodium hydroxide solution (50 mL) was added, and ethyl acetate (25 mL×2)The combined organic layers were dried with anhydrous sodium sulfate, filtered and evaporated.
87.31 % ee
With (+)-(1S)-camphor-10-sulphonic acid In ethanol for 2 h;
3-phenylpiperidine (1,100 g, 621.1 mmol)Soluble in ethanol (50mL),Will be dissolved in D-camphorsulfonic acid (145.8g, 622.2mmol)A solution of ethanol (150 mL) was added dropwise to a solution of the racemic 3-phenylpiperidine in ethanol and stirred for 2 h.Filtration to obtain camphor sulfonate; then, adding methanol (5 L) to the camphor sulfonate,After heating to complete dissolution, the stirring was stopped; the temperature was slowly lowered to room temperature, and crystallization was carried out at 0 ° C for 2 days.Filtration gave a crude white solid, 1N aqueous sodium hydroxide (50 mL).Extracted with ethyl acetate (25 mL x 2), and the organic phases were combined.Dry over anhydrous sodium sulfate, filtered and concentrated to give a white solid.Namely (R)-3-phenylpiperidine, the yield was 19.3percent.
Reference：
[1] Patent: CN108203404, 2018, A, . Location in patent: Paragraph 0143-0146
[2] Patent: CN108203404, 2018, A, . Location in patent: Paragraph 0163-0166
3
[ 40114-49-6 ]
[ 59349-71-2 ]
Reference：
[1] Patent: CN108203404, 2018, A,
[2] Patent: CN108203404, 2018, A,
[3] Patent: CN108203404, 2018, A,
[4] Patent: CN108203404, 2018, A,
[5] Patent: CN108203404, 2018, A,
[6] Patent: CN108203404, 2018, A,
[7] Patent: CN108203404, 2018, A,
[8] Patent: CN108203404, 2018, A,
4
[ 100-59-4 ]
[ 59349-71-2 ]
Reference：
[1] Patent: CN108203404, 2018, A,
[2] Patent: CN108203404, 2018, A,
[3] Patent: CN108203404, 2018, A,
[4] Patent: CN108203404, 2018, A,
5
[ 58879-07-5 ]
[ 59349-71-2 ]
Reference：
[1] Patent: CN108203404, 2018, A,
[2] Patent: CN108203404, 2018, A,
[3] Patent: CN108203404, 2018, A,
[4] Patent: CN108203404, 2018, A,
6
[ 100-58-3 ]
[ 59349-71-2 ]
Reference：
[1] Patent: CN108203404, 2018, A,
[2] Patent: CN108203404, 2018, A,
[3] Patent: CN108203404, 2018, A,
[4] Patent: CN108203404, 2018, A,
7
[ 3979-67-7 ]
[ 59349-71-2 ]
Reference：
[1] Patent: CN108203404, 2018, A,
[2] Patent: CN108203404, 2018, A,
8
[ 3973-62-4 ]
[ 59349-71-2 ]
[ 430461-56-6 ]
Yield
Reaction Conditions
Operation in experiment
89.19 % ee
With (R)-10-camphorsulfonic acid In ethanol for 2 h;
3-Phenylpiperidine (1,100 g, 621.1 mmol) was dissolved in isopropanol (50 mL).Will be dissolved in L-tartaric acid (93.16g, 622.2mmol)Isopropyl alcohol (200mL)The solution was added dropwise to a solution of racemic 3-phenylpiperidine in isopropanol and stirred for 2 h.Filtration to obtain tartrate;Then, methanol (10 L) was added to the tartrate, and after heating to complete dissolution, the stirring was stopped; the temperature was slowly lowered to room temperature, and the mixture was crystallized at -20 ° C for 7 days, and filtered to obtain a crude white solid.A 1N aqueous sodium hydroxide solution (50 mL) was added, and ethyl acetate (25 mL×2)The combined organic layers were dried with anhydrous sodium sulfate, filtered and evaporated.
87.31 % ee
With (+)-(1S)-camphor-10-sulphonic acid In ethanol for 2 h;
3-phenylpiperidine (1,100 g, 621.1 mmol)Soluble in ethanol (50mL),Will be dissolved in D-camphorsulfonic acid (145.8g, 622.2mmol)A solution of ethanol (150 mL) was added dropwise to a solution of the racemic 3-phenylpiperidine in ethanol and stirred for 2 h.Filtration to obtain camphor sulfonate; then, adding methanol (5 L) to the camphor sulfonate,After heating to complete dissolution, the stirring was stopped; the temperature was slowly lowered to room temperature, and crystallization was carried out at 0 ° C for 2 days.Filtration gave a crude white solid, 1N aqueous sodium hydroxide (50 mL).Extracted with ethyl acetate (25 mL x 2), and the organic phases were combined.Dry over anhydrous sodium sulfate, filtered and concentrated to give a white solid.Namely (R)-3-phenylpiperidine, the yield was 19.3percent.
Reference：
[1] Patent: CN108203404, 2018, A, . Location in patent: Paragraph 0143-0146
[2] Patent: CN108203404, 2018, A, . Location in patent: Paragraph 0163-0166
With (R)-10-camphorsulfonic acid; In ethanol; for 2h;
<strong>[3973-62-4]3-Phenylpiperidine</strong> (1,100 g, 621.1 mmol) was dissolved in isopropanol (50 mL).Will be dissolved in L-tartaric acid (93.16g, 622.2mmol)Isopropyl alcohol (200mL)The solution was added dropwise to a solution of racemic <strong>[3973-62-4]3-phenylpiperidine</strong> in isopropanol and stirred for 2 h.Filtration to obtain tartrate;Then, methanol (10 L) was added to the tartrate, and after heating to complete dissolution, the stirring was stopped; the temperature was slowly lowered to room temperature, and the mixture was crystallized at -20 C for 7 days, and filtered to obtain a crude white solid.A 1N aqueous sodium hydroxide solution (50 mL) was added, and ethyl acetate (25 mL×2)The combined organic layers were dried with anhydrous sodium sulfate, filtered and evaporated.
With (+)-(1S)-camphor-10-sulphonic acid; In ethanol; for 2h;
<strong>[3973-62-4]3-phenylpiperidine</strong> (1,100 g, 621.1 mmol)Soluble in ethanol (50mL),Will be dissolved in D-camphorsulfonic acid (145.8g, 622.2mmol)A solution of ethanol (150 mL) was added dropwise to a solution of the racemic <strong>[3973-62-4]3-phenylpiperidine</strong> in ethanol and stirred for 2 h.Filtration to obtain camphor sulfonate; then, adding methanol (5 L) to the camphor sulfonate,After heating to complete dissolution, the stirring was stopped; the temperature was slowly lowered to room temperature, and crystallization was carried out at 0 C for 2 days.Filtration gave a crude white solid, 1N aqueous sodium hydroxide (50 mL).Extracted with ethyl acetate (25 mL x 2), and the organic phases were combined.Dry over anhydrous sodium sulfate, filtered and concentrated to give a white solid.Namely (R)-<strong>[3973-62-4]3-phenylpiperidine</strong>, the yield was 19.3%.
With L-Tartaric acid; In isopropyl alcohol; for 2h;
<strong>[3973-62-4]3-Phenylpiperidine</strong> (1,100 g, 621.1 mmol) was dissolved in isopropanol (50 mL).Will be dissolved in L-tartaric acid (93.16g, 622.2mmol)Isopropyl alcohol (200mL)The solution was added dropwise to a solution of racemic <strong>[3973-62-4]3-phenylpiperidine</strong> in isopropanol and stirred for 2 h.Filtration to obtain tartrate;Then, methanol (10 L) was added to the tartrate, and after heating to complete dissolution, the stirring was stopped; the temperature was slowly lowered to room temperature, and the mixture was crystallized at -20 C for 7 days, and filtered to obtain a crude white solid.A 1N aqueous sodium hydroxide solution (50 mL) was added, and ethyl acetate (25 mL×2)The combined organic layers were dried with anhydrous sodium sulfate, filtered and evaporated.
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