Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol under 760 Torr; for 5h; | 96% |
(S)-1-Pyrrolidin-2-yl-methanol
D-Prolin
Conditions | Yield |
---|---|
With potassium permanganate In water at 15 - 20℃; Concentration; | 95.65% |
D-Prolin
Conditions | Yield |
---|---|
With hydrogen; palladium(II) hydroxide In tetrahydrofuran; methanol at 20℃; for 3h; | 83% |
With hydrogen; palladium(II) hydroxide In tetrahydrofuran; methanol at 20℃; for 3h; | 83% |
D-Prolin
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol | 77% |
(R)-N-(3,5-dinitrobenzoyl)proline
D-Prolin
Conditions | Yield |
---|---|
With hydrogenchloride | |
With hydrogenchloride |
(2R,5R)-2-t-butyl-1-t-butyloxycarbonyl-5-(3-chloropropyl)-3-methyl-4-imidazolidinone
D-Prolin
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
(2S,3S)-2,3-Dihydroxy-succinic acid; compound with (R)-pyrrolidine-2-carboxylic acid
D-Prolin
Conditions | Yield |
---|---|
With ammonium hydroxide 1.) methanol, 0.5 h; Yield given. Multistep reaction; |
(S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide
acrolein
A
L-proline
B
D-Prolin
Conditions | Yield |
---|---|
With sodium tetrahydroborate; triethylamine; nickel(II) nitrate Yield given. Multistep reaction. Yields of byproduct given; |
D-Prolin
Conditions | Yield |
---|---|
With hydrogenchloride; nitrosylchloride Erhitzen des Reaktionsprodukts mit wss. Ba(OH)2; |
D-Prolin
Conditions | Yield |
---|---|
With Cinchonin |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium cyanoborohydride; triethylamine 1.) MeOH, 60 deg C; 2.) EtOH, 80 deg C; 3.) MeOH, r.t., 24 h; Yield given. Multistep reaction; |
acrolein
A
(S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide
B
L-proline
C
D-Prolin
Conditions | Yield |
---|---|
With sodium tetrahydroborate; triethylamine 1.) MeOH, -10 deg C, 2.) water, 25 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
N-benzyloxycarbonyl-L-phenylalanyl-D-proline
A
N-Cbz-L-Phe
B
D-Prolin
Conditions | Yield |
---|---|
With hydrogenchloride; carboxypeptisae-A In water at 37℃; pH=6.5; Enzyme kinetics; Kinetics; Further Variations:; Reagents; |
D-Prolin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. HCl / Heating 2: 77 percent / H2 / Pd/C / methanol View Scheme |
D-Prolin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aq. HCl / Heating 2: aq. HCl / Heating 3: 77 percent / H2 / Pd/C / methanol View Scheme |
methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate
D-Prolin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 91 percent / NaN3 / dimethylformamide / 12 h / 100 °C 2: 82 percent / DIBAL / light petroleum; toluene; hexane / 1 h / -78 °C 3: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature 4: 82 percent / NaHCO3 / aq. ethanol 5: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature 6: 79 percent / aq. NaIO4 / methanol / 2 h 7: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h 8: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr View Scheme |
(2R)-(+)-phenylmethyl 2-formylpyrrolidine-1-carboxylate
D-Prolin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h 2: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr View Scheme |
(R)-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]pyrrolidine
D-Prolin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 82 percent / NaHCO3 / aq. ethanol 2: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature 3: 79 percent / aq. NaIO4 / methanol / 2 h 4: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h 5: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr View Scheme |
(R)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde
D-Prolin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature 2: 82 percent / NaHCO3 / aq. ethanol 3: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature 4: 79 percent / aq. NaIO4 / methanol / 2 h 5: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h 6: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr View Scheme |
(R)-1-benzyloxycarbonyl-2-[(S)-1,2-dihydroxyethyl]pyrrolidine
D-Prolin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 79 percent / aq. NaIO4 / methanol / 2 h 2: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h 3: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr View Scheme |
(R)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester
D-Prolin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 82 percent / DIBAL / light petroleum; toluene; hexane / 1 h / -78 °C 2: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature 3: 82 percent / NaHCO3 / aq. ethanol 4: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature 5: 79 percent / aq. NaIO4 / methanol / 2 h 6: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h 7: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr View Scheme |
(2R,4'S)-N-Benzyloxycarbonyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)pyrrolidine
D-Prolin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature 2: 79 percent / aq. NaIO4 / methanol / 2 h 3: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h 4: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr View Scheme |
1-(3,5-dinitro-benzoyl)-DL-proline
D-Prolin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: brucine; acetone 2: aqueous HCl View Scheme |
Conditions | Yield |
---|---|
With pyridine; H2; CO In tetrahydrofuran; hydrogenchloride |
Conditions | Yield |
---|---|
With pyridine; H2; CO; Co2(CO)8 In tetrahydrofuran; hydrogenchloride |
Conditions | Yield |
---|---|
With C24H29CoN2O4 In dichloromethane; water at 10℃; for 24h; Resolution of racemate; optical yield given as %ee; | |
Stage #1: rac-Pro-OH With C24H29CoN2O4 In dichloromethane; water at 10℃; for 24h; Resolution of racemate; Stage #2: With sodium dithionite In dichloromethane; water for 5h; Resolution of racemate; optical yield given as %ee; | |
With shaking calcined L-Pro chiral ordered mesoporous silica Resolution of racemate; |
Conditions | Yield |
---|---|
With potassium permanganate; sulfuric acid In water at 0 - 20℃; optical yield given as %ee; |
Conditions | Yield |
---|---|
With hydrogenchloride; water at 150℃; for 12h; |
apratoxin S5
A
N-methylalanine
B
N-methyl-L-isoleucine
C
O-Methyltyrosine
D
D-Prolin
Conditions | Yield |
---|---|
With hydrogenchloride; water at 110℃; for 24h; |
Conditions | Yield |
---|---|
With thionyl chloride at 0℃; for 2h; | 100% |
With thionyl chloride Reflux; | 97% |
In dimethyl sulfoxide at 10 - 80℃; for 2h; | 88% |
Conditions | Yield |
---|---|
With sodium hydroxide | 100% |
Conditions | Yield |
---|---|
With sodium hydroxide In water; toluene at 20℃; for 1h; Inert atmosphere; | 100% |
With sodium hydroxide In water at 0 - 20℃; | 93% |
With sodium hydroxide In water Ambient temperature; |
Conditions | Yield |
---|---|
With thionyl chloride at 20℃; for 16.5h; | 100% |
Conditions | Yield |
---|---|
With thionyl chloride In methanol Reflux; | 100% |
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 1h; | 100% |
D-Prolin
Methacryloyl chloride
(2R)-1-methacryloylpyrrolidin-2-carboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide In acetone at 0℃; for 0.5h; | 99% |
With sodium hydroxide In tetrahydrofuran; acetone at 5 - 20℃; for 3h; pH=11 - 12; Cooling with ice; | 83.8% |
With sodium hydroxide In acetone at 20℃; for 4h; pH=10.3; | 81% |
Conditions | Yield |
---|---|
With porcine kidney D-amino acid oxidase (EC 1.4.3.3.); sodium cyanoborohydride; flavin adenine dinucleotide In phosphate buffer at 37℃; | 99% |
4-Fluoro-2-hydroxyacetophenone
D-Prolin
(R)-1-(4-acetyl-3-hydroxyphenyl)pyrrolidine-2-carboxylic acid
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 95℃; for 2.5h; | 99% |
Conditions | Yield |
---|---|
Stage #1: D-Prolin With pyridine; chloro-trimethyl-silane In dichloromethane for 1.16667h; Stage #2: n-dodecanoyl chloride In dichloromethane at 0 - 20℃; for 1.83333h; | 99% |
Conditions | Yield |
---|---|
With triethylamine | 98% |
With triethylamine In dichloromethane at 25 - 30℃; | 97% |
Stage #1: D-Prolin With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 0.5h; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 0 - 20℃; | 95% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 3750.38 Torr; for 5h; Inert atmosphere; | 98% |
D-Prolin
N-nitroso-D-proline
Conditions | Yield |
---|---|
With 3,3-dimethyl-2-nitroso-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide In dichloromethane at 20℃; Sealed tube; | 98% |
tetra-n-butylphosphonium hydroxide
D-Prolin
Conditions | Yield |
---|---|
In water at 20℃; for 2h; | 97% |
Conditions | Yield |
---|---|
With sodium methylate In methanol at 20℃; for 12h; Darkness; | 97% |
With sodium methylate In methanol at 50℃; for 24h; Inert atmosphere; diastereoselective reaction; |
1-Naphthalenesulfonyl chloride
D-Prolin
(R)-1-(naphthalen-1-ylsulfonyl)pyrrolidine-2-carboxylic acid
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 50℃; for 5h; | 96.2% |
Conditions | Yield |
---|---|
With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 3.75h; | 96% |
With potassium carbonate In water 1) 0 deg C, 1 h, 2) r.t., 2 h; Yield given; | |
Stage #1: chloroformic acid ethyl ester; D-Prolin With sodium hydroxide; water at 0 - 20℃; pH=9 - 10; Stage #2: With hydrogenchloride; water at 0℃; pH=1; |
isatoic anhydride
D-Prolin
(11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 180℃; Condensation; | 96% |
In dimethyl sulfoxide at 150℃; for 2h; Inert atmosphere; | 82% |
In dimethyl sulfoxide at 100℃; for 5h; | 81% |
Conditions | Yield |
---|---|
Stage #1: formaldehyd; D-Prolin Stage #2: With hydrogen | 96% |
With hydrogen; palladium 10% on activated carbon In methanol under 775.743 Torr; for 18h; | 96% |
With hydrogen; palladium 10% on activated carbon In methanol under 775.743 Torr; for 18h; | 96% |
Conditions | Yield |
---|---|
In n-heptane at 20℃; for 48h; Inert atmosphere; | 96% |
dimethylsulfite
toluene-4-sulfonic acid
D-Prolin
(D)-proline, methyl ester, tosylate salt
Conditions | Yield |
---|---|
In diethyl ether at 90℃; for 7h; | 95% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide In water; acetone | 95% |
2-(3-fluoro-6-nitrophenyl)benzothiazole
D-Prolin
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran; water for 16h; Reflux; | 95% |
Conditions | Yield |
---|---|
With dmap at 20℃; for 5.16667h; Reagent/catalyst; | 94.8% |
D-Prolin
tetrabutylammonium (R)-prolinate
Conditions | Yield |
---|---|
In water at 100℃; for 65h; | 94% |
tetra-n-butylphosphonium hydroxide
D-Prolin
Conditions | Yield |
---|---|
In water at 100℃; for 24h; | 94% |
Conditions | Yield |
---|---|
Stage #1: Cbz-Gly-ONSuc; D-Prolin With N-ethyl-N,N-diisopropylamine In ethyl acetate for 12h; Inert atmosphere; Green chemistry; Stage #2: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In ethyl acetate for 0.5h; Inert atmosphere; Green chemistry; Stage #3: L-glutamic dimethyl ester hydrochloride In ethyl acetate for 1h; Inert atmosphere; Green chemistry; chemoselective reaction; | 94% |
perfluoro-1-butanesulfonyl fluoride
D-Prolin
(R)-1-(butylsulfonyl)pyrrolidine-2-carboxylic acid
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 50℃; for 5h; | 93.1% |
Molecular Structure of D-Proline (CAS NO.344-25-2):
IUPAC Name: (2R)-pyrrolidin-1-ium-2-carboxylate
Empirical Formula: C5H9NO2
Molecular Weight: 115.1305
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 29.54 Å2
Index of Refraction: 1.487
Molar Refractivity: 27.9 cm3
Molar Volume: 96.9 cm3
Surface Tension: 43.4 dyne/cm
Density: 1.186 g/cm3
Flash Point: 106.3 °C
Enthalpy of Vaporization: 53.9 kJ/mol
Boiling Point: 252.2 °C at 760 mmHg
Vapour Pressure: 0.00615 mmHg at 25°C
EINECS: 206-452-7
Melting point:223 °C (dec.)(lit.)
Alpha: 84.75 o (C=4, H2O)
Refractive index: 85 ° (C=4, H2O)
Storage temp: Store at RT
Water Solubility: soluble >1000 g/L (20 oC)
Melting point: 223 °C (dec.)(lit.)
Product Categories: Amino Acids series; Miscellaneous Biochemicals; Proline [Pro, P]; Amino Acids and Derivatives; alpha-Amino Acids; Amino Acids;Biochemistry; Amino Acids and Derivatives
D-Proline (CAS NO.344-25-2) is used as synthesizing the drugs.
Hazard Codes of D-Proline (CAS NO.344-25-2): Xi,Xn
Risk Statements: 22-36/37/38
R22: Harmful if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36/37/39-26
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
F: 3-10
Hazard Note: Irritant
D-Proline , with CAS number of 344-25-2, can be called (2R)-2-Pyrrolidinecarboxylic acid ; (R)-(+)-Proline ; (+)-(R)-Proline ; (R)-Proline ; (R)-Pyrrolidine-2-carboxylic acid ; D-(+)-Proline; D-Pyrrolidine-2-carboxylic acid ; (R)-pyrrolidine-2-carboxylic acid . It is a white to off-white powder.
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