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[ CAS No. 114883-82-8 ] {[proInfo.proName]}

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Chemical Structure| 114883-82-8
Chemical Structure| 114883-82-8
Structure of 114883-82-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 114883-82-8 ]

CAS No. :114883-82-8 MDL No. :MFCD19704703
Formula : C7H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WBXUFOSSZLFNPQ-ZCFIWIBFSA-N
M.W : 143.18 Pubchem ID :20803296
Synonyms :
Chemical Name :(R)-Methyl 1-methylpyrrolidine-2-carboxylate

Calculated chemistry of [ 114883-82-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.74
TPSA : 29.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : -0.4
Log Po/w (WLOGP) : -0.13
Log Po/w (MLOGP) : 0.35
Log Po/w (SILICOS-IT) : 0.5
Consensus Log Po/w : 0.49

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.34
Solubility : 64.9 mg/ml ; 0.453 mol/l
Class : Very soluble
Log S (Ali) : 0.24
Solubility : 251.0 mg/ml ; 1.75 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.53
Solubility : 41.9 mg/ml ; 0.292 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 114883-82-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 114883-82-8 ]

* 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.

  • Downstream synthetic route of [ 114883-82-8 ]

[ 114883-82-8 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 151-50-8 ]
  • [ 114883-82-8 ]
  • [ 20297-37-4 ]
  • 2
  • [ 151-50-8 ]
  • [ 114883-82-8 ]
  • N-methyl-2-methoxycarbonyl-2-cyanopyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride Yield given. Multistep reaction;
  • 3
  • [ 114883-82-8 ]
  • [ 250672-50-5 ]
  • [ 250672-54-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(tert-butyldimethylsilyl)-3-bromo-5-methoxy-1H-indole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: N-methyl-D-proline methyl ester In tetrahydrofuran; hexane at -78℃; for 9h;
  • 4
  • [ 114883-82-8 ]
  • [ 250672-59-4 ]
  • [ 250672-62-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-bromo-1-(tert-butyldimethylsilyl)-4-benzyloxyindole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: N-methyl-D-proline methyl ester In tetrahydrofuran; hexane at -78℃; for 20h;
  • 5
  • [ 114883-82-8 ]
  • [ 126373-97-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) 30percent H2O2, 2.) Pd/C, 3.) trifluoroacetic anhydride 2: 25 percent / aq. NaOH / 24 h
  • 6
  • [ 114883-82-8 ]
  • [ 45771-52-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) 30percent H2O2, 2.) Pd/C, 3.) trifluoroacetic anhydride 2: 20 percent / aq. NaOH / 24 h
  • 7
  • [ 50-00-0 ]
  • [ 43041-12-9 ]
  • [ 114883-82-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: formaldehyd; methyl (2R)-pyrrolidine-2-carboxylate With sodium tris(acetoxy)borohydride In DMF (N,N-dimethyl-formamide); water for 12h; Stage #2: With sodium hydrogencarbonate In water 53.A Intermediate 53: (2R)-N-Methyl-prolinecarboxyaldehyde Step A: (2R) -N-Methyl-proline methyl ester To a solution of (2R)-Proline methylester (1.20 g, 10.0 mmol) and formalin (37 % in H2O, 1.12 mL, 15.0 mmol) in DMF (30 mL) was added NaBH (OAc) 3 (4.20 g, 20.0 mmol). After being stirred for 12h, the reaction mixture was concentrated in vacuo, and the residue was diluted with NaHC03 (30 mL). The organic material was extracted with EtOAc, and the extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by column chromatography (eluent: EtOAc/Hex = 4/1) to give the title compound. MS [M+H] = 144 (M+1)
Stage #1: formaldehyd; methyl (2R)-pyrrolidine-2-carboxylate In water at 0℃; for 0.25h; Stage #2: With sodium tetrahydroborate In water at 0 - 20℃; for 3h; Stage #3: With sodium carbonate In water 2.C Method C To a solution of sulfuric acid (3.5 mi, 65.3 mmol) in methanol (45 ml) was added D- proline (10.0 g, 86.9 mmol). The mixture was refluxed with stirring for 18 h. The solution was then cooled to 0°C and neutralised by addition of aqueous potassium carbonate (2. 5 M; 10 ml). Formaldehyde (37% solution in water; 11 ml, 136 mmol) was added and the mixture stirred at 0°C for 15 minutes. Sodium borohydride (1.6 g, 42.3 mmol) was added at 0°C and the mixture was stirred at room temperature for 3 h. The precipitate was filtered off and the filtrate was partitioned between dichloro- methane and water. The isolated aqueous layer was adjusted to pH 10 using solid sodium carbonate and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford crude (R)-1- methylpyrrolidine-2-carboxylic acid methyl ester (13.13 g). A portion of this crude product (5. 0 g) was purified by flash column chromatography eluting with 0-2% (v/v) methanol in dichloromethane to afford (R)-1-methylpyrrolidine- 2-carboxylic acid methyl ester (1. 30 g).
  • 8
  • [ 114883-82-8 ]
  • [ 852324-28-8 ]
YieldReaction ConditionsOperation in experiment
With diisobutylaluminium hydride In dichloromethane at -30℃;
Multi-step reaction with 2 steps 1.1: sodium tetrahydridoborate; ethanol 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -70 °C 2.2: -70 °C
  • 9
  • [ 114883-82-8 ]
  • [ 74-88-4 ]
  • [ 1408363-91-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-methyl-D-proline methyl ester With potassium carbonate In acetonitrile at 20℃; for 1.5h; Stage #2: methyl iodide In acetonitrile
  • 10
  • tetrafluoroboric acid [ No CAS ]
  • [ 3140-73-6 ]
  • [ 114883-82-8 ]
  • C12H19N4O4(1+)*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: tetrafluoroboric acid; N-methyl-D-proline methyl ester In diethyl ether; dichloromethane Stage #2: 2-chloro-4,6-dimethoxy-1 ,3,5-triazine With sodium hydrogencarbonate In acetonitrile at 20℃; Synthesis of L-5b (DMT/L-N-MePro-OMe/BF4-)from L-N-methylproline methyl ester tetrafluoroborateand CDMT General procedure: To the solution of L-N-methylproline methyl ester (5.50 g; 39 mmol) in dichloromethane (50 mL)equimolar amount of HBF4 in ether (4.02 mL; 39mmol) was added. Solvent was removed under reduced pressure yielding quantitatively L-Nmethylprolinemethyl ester tetrafluoroborate as white solid. Solid residue was dissolved in acetonitrile(100 mL), anhydrous NaHCO3 (6.10 g; 72mmol) and CDMT (6.30 g; 39 mmol) were addedand suspension was vigorously stirred at room temperature until all CDMT was consumed as monitoredby TLC. The suspension was filtered. The filtercake was washed several times with acetonitrile and combined filtrates were evaporated under reduced pressure affording 5b (DMT/L-N-MePro-OMe/BF4-) (12.0 g, yield 83%) as pale oil.
  • 11
  • [ 114883-82-8 ]
  • (R)-1-methyl-2-pyrrolidinemethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.8% With sodium tetrahydridoborate In ethanol 5-6 Synthesis of Intermediate Z3 Add 60g (0.522mol) of intermediate Z2 to the reaction vessel, add 400ml of absolute ethanol to dissolve, add 20g of sodium borohydride (0.529mol), react for 3 to 4 hours, add dilute hydrochloric acid to quench the reaction, adjust with 4N sodium hydroxide pH value reached 8-9, filtered, the filtrate was concentrated, sodium chloride was added to saturation, tetrahydrofuran was added for extraction, after separation, the organic layer was concentrated to dryness to obtain 54.5 g of yellow oil Z3, yield 90.8%.
90.8% With sodium tetrahydridoborate; ethanol 5; 6 Synthesis of the intermediate Z3 In the reaction vessel, the intermediate Z2 60g (0.522mol) was added, 400ml of absolute ethanol was added to dissolve, 20g of sodium borohydride (0.529mol) was added, the reaction was added for 3 to 4 hours, dilute hydrochloric acid quenching reaction was added, pH was adjusted with 4N sodium hydroxide to 8 to 9, filtered, filtrate was concentrated, sodium chloride was added to saturation, tetrahydrofuran extraction was added, after stratification, the organic layer was concentrated to dry, giving the yellow oilY Z3 54.5g, yield 90.8%.
  • 12
  • [ 114883-82-8 ]
  • C10H17NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium tetrahydridoborate / ethanol 2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / -70 °C 2.2: -70 °C 2.3: 20 °C
Multi-step reaction with 3 steps 1.1: sodium tetrahydridoborate; ethanol 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -70 °C 2.2: -70 °C 3.1: dichloromethane / 20 °C
  • 13
  • [ 114883-82-8 ]
  • C8H13NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium tetrahydridoborate / ethanol 2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / -70 °C 2.2: -70 °C 2.3: 20 °C 3.1: sodium hydroxide / 40 - 50 °C
Multi-step reaction with 4 steps 1.1: sodium tetrahydridoborate; ethanol 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -70 °C 2.2: -70 °C 3.1: dichloromethane / 20 °C 4.1: sodium hydroxide / 40 - 50 °C
  • 14
  • [ 344-25-2 ]
  • [ 114883-82-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 16 h / 50 °C 2: dichlorosulfoxide / lithium hydroxide monohydrate / Reflux
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 16 h / 50 °C 2: dichlorosulfoxide / Reflux
  • 15
  • [ 67-56-1 ]
  • (2R)-1-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 114883-82-8 ]
YieldReaction ConditionsOperation in experiment
95% With dichlorosulfoxide In lithium hydroxide monohydrate Reflux; 2-4 Synthesis of Intermediate Z2 Intermediate Z1 56g (0.434mol), add 300ml methanol, intermediate Z1 has good solubility in methanol and water, so choose methanol as solvent, stir to dissolve, slowly add 62g (0.52mol) thionyl chloride dropwise, reflux reaction After monitoring the reaction by thin-layer chromatography, the reaction solution was concentrated, and 100 ml of ethyl acetate was added, and the pH value was adjusted to 9-10 with 4N sodium hydroxide. After layering, the aqueous layer was extracted with 100 ml of ethyl acetate, and the organic layers were combined. After drying, it was spin-dried to obtain 59 g of yellow oil Z2 with a yield of 95%.
95% With dichlorosulfoxide Reflux; 2; 3; 4 Synthesis of the intermediate Z2 Intermediate Z1 56g (0.434mol), add 300ml of methanol, intermediate Z1 is better soluble in methanol and water, so choose methanol as a solvent, stir to dissolve, slowly add 62g (0.52mol) dichlorosulfoxide, reflux reaction to thin layer chromatography monitoring reaction completely, after the reaction solution is concentrated, add 100ml of ethyl acetate, adjust the pH value with 4N sodium hydroxide to 9 ~ 10, after layering, the water layer is then extracted with 100ml of ethyl acetate, combined with the organic layer, After drying, it was dried to give a yellow oily Z2 59g with a yield of 95%.
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