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[ CAS No. 51535-00-3 ]

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2D
Chemical Structure| 51535-00-3
Chemical Structure| 51535-00-3
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Product Details of [ 51535-00-3 ]

CAS No. :51535-00-3MDL No. :MFCD00003196
Formula : C13H15NO3 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :233.26Pubchem ID :98909
Synonyms :

Computed Properties of [ 51535-00-3 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 51535-00-3 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P264-P270-P301+P312-P330UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51535-00-3 ]

  • Upstream synthesis route of [ 51535-00-3 ]
  • Downstream synthetic route of [ 51535-00-3 ]

[ 51535-00-3 ] Synthesis Path-Upstream   1~8

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YieldReaction ConditionsOperation in experiment
99.14%
Stage #1: With dimethylsulfide; borane In toluene at 0 - 110℃; for 16 h; Heating / reflux
Stage #2: With sodium hydrogencarbonate In water; toluene at -10 - 20℃; for 2 h; Heating / reflux
Example A: Synthesis of (l-benzvl-pyrrolidin-3-vlmethvl)-methyl-amineStep a: Synthesis of l-(benzyl-pyrrolidin-3-yI)-methanolA solution of the compound l-benzyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (1.0 eq.) (commercially available) in toluene was cooled to 0°C under inert atmosphere. To the mixture was added solution of borane (3.75 eq.) in dimethyl sulphideand refluxed the mixture for 16 hours at 100°-110°C. The resulting reaction mixture was cooled to room temperature and subsequently to -5° to -10°C followed by the addition of sodium bicarbonate solution dropwise. The mixture was slowly brought to room temperature and subsequently refluxed the reaction mixture for 2 hours. The mixture was cooled and organic layer was separated. Aqueous layer was extracted with toluene. The combined toluene layers were washed with water and brine solution. The organic solvent was evaporated under reduced pressure to furnish the title compound. Yield: 99.14percent.
61% With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 2.5 h; Heating / reflux Compound b was prepared by a similar procedure to Wu's (J. Org. Chem. 1961, 1519.) except using THF to dissolve methyl l-benzyl-5-oxo-3pyrrolidinecarboxylate: [0388] A solution of methyl 1-benzyl-5-oxo-3pyrrolidinecarboxylate (a) (8.00 g, 34.30 mmol) in 10 mL of anhydrous THF was slowly added to a slurry of powdered lithium aluminum hydride (1.82 g, 48.01 mmol) in 30 mL of absolute ether. The addition was made over a period of 0.5 hour with efficient stirring so as to maintain a moderate reflux rate. When the addition was complete, refluxing and stirring was continued for 2 hours, after which the reaction mixture was left at room temperature. The mixture was quenched with 3 mL of water, and stirred for 2 hours. The white precipitate was filtered and washed with 2.x.30 mL of ether. The solid was extracted with Soxhlet type apparatus in EtOH for 8 hours. Th EtOH was removed. The residue was washed with Et2O (3.x.20 mL). The Et2O solutions were combined, dried over MgSO4, and concentrated. The residue was distilled under vacuum. The fraction at 137-145° C./1 mmHg was collected to give compound b (4.0 g) as a colorless oil.
Reference: [1] Patent: WO2006/18708, 2006, A2, . Location in patent: Page/Page column 21-22
[2] Letters in Organic Chemistry, 2011, vol. 8, # 3, p. 155 - 162
[3] Patent: US2004/147502, 2004, A1, . Location in patent: Page/Page column 36-37
[4] Organic Letters, 1999, vol. 1, # 5, p. 799 - 801
[5] Patent: US2005/165005, 2005, A1, . Location in patent: Page/Page column 59-60
[6] Patent: US6498165, 2002, B1,
[7] Patent: US6562811, 2003, B1,
[8] Patent: US4923857, 1990, A,
[9] Patent: EP1221441, 2002, A2, . Location in patent: Page 43, 197
[10] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 18, p. 5440 - 5443
[11] Patent: WO2006/123725, 2006, A1, . Location in patent: Page/Page column 63
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Reference: [1] Patent: US6329380, 2001, B1,
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Reference: [1] Patent: US2003/27822, 2003, A1,
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Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 9, p. 2005 - 2009
[2] Tetrahedron Letters, 1999, vol. 40, # 19, p. 3673 - 3676
[3] European Journal of Organic Chemistry, 2005, # 4, p. 673 - 682
[4] Journal of Medicinal Chemistry, 1999, vol. 42, # 25, p. 5254 - 5265
[5] Organic Letters, 1999, vol. 1, # 5, p. 799 - 801
[6] Patent: US2003/229226, 2003, A1, . Location in patent: Page 14
[7] Patent: WO2004/14910, 2004, A1, . Location in patent: Page 69-70
[8] Patent: EP307140, 1989, A1,
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YieldReaction ConditionsOperation in experiment
3% With hydrogenchloride; sodium hydroxide In tetrahydrofuran; dichloromethane EXAMPLE 218
1-[1-(Anthracene-9-carbonyl)-piperidin-4-yl]-pyrrolidine-3-carboxylic acid diethylamide
To a solution of 1-benzyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (30 mmol, 7 g) in anhydrous tetrahydrofuran (40 ml) was added borane-tetrahydrofuran solution (1M, 50 mmol, 50 mL) at ambient temperature.
When gas evolution had subsided the solution was heated under reflux for 75 min then stirred for 16 hr at ambient temperature.
Hydrochloric acid (6M) was added dropwise (ca. 5 mL) and the mixture was stirred at ambient temperature for 1 hr before removing the solvent under vacuum.
The residue was dissolved in dichloromethane and the solution was washed with dilute sodium hydroxide solution.
The dichloromethane solution was then extracted with dilute hydrochloric acid (*3), the extracts combined, made basic by addition of sodium hydroxide and extracted with dichloromethane (*3).
The combined organic extract was dried over anhydrous sodium sulfate and the solvent was removed under vacuum.
The product was purified by chromatography on silica gel eluding with 5percent methanol-dichloromethane to give 1-benzyl-pyrrolidine-3-carboxylic acid methyl ester (200 mg, 3percent).
MS: 220.2 [M+H]+
Reference: [1] Patent: US2003/187254, 2003, A1,
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Reference: [1] European Journal of Organic Chemistry, 2005, # 4, p. 673 - 682
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Reference: [1] Patent: EP1403255, 2004, A1,
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Reference: [1] Patent: EP1403255, 2004, A1,
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