[ CAS No. 5291-77-0 ] {[proInfo.proName]}

Name: 5291-77-0|1-Benzylpyrrolidin-2-one|98%
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Quality Control of [ 5291-77-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 5291-77-0 ]

Product Details of [ 5291-77-0 ]

CAS No. :	5291-77-0	MDL No. :	MFCD00003195
Formula :	C₁₁H₁₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LVUQCTGSDJLWCE-UHFFFAOYSA-N
M.W :	175.23	Pubchem ID :	79176
Synonyms :

Calculated chemistry of [ 5291-77-0 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.53
TPSA :	20.31 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.13
Log Po/w (XLOGP3) :	1.25
Log Po/w (WLOGP) :	1.28
Log Po/w (MLOGP) :	1.78
Log Po/w (SILICOS-IT) :	2.35
Consensus Log Po/w :	1.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.92
Solubility :	2.09 mg/ml ; 0.0119 mol/l
Class :	Very soluble
Log S (Ali) :	-1.27
Solubility :	9.31 mg/ml ; 0.0531 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.13
Solubility :	0.129 mg/ml ; 0.000738 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 5291-77-0 ]

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

Application In Synthesis of [ 5291-77-0 ]

* 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 [ 5291-77-0 ]

[ 5291-77-0 ] Synthesis Path-Downstream 1~62

1
[ 96-48-0 ]
[ 100-46-9 ]
[ 5291-77-0 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 8627 - 8630
[2]Tetrahedron,2004,vol. 60,p. 4567 - 4578
[3]Journal of Organic Chemistry,2015,vol. 80,p. 4152 - 4156
[4]Chemische Berichte,1936,vol. 69,p. 2727,2729
[5]Justus Liebigs Annalen der Chemie,1955,vol. 596,p. 1,205
[6]Journal of the American Chemical Society,1947,vol. 69,p. 715

2
[ 22813-61-2 ]
[ 5291-77-0 ]

Reference： [1]Heterocycles,1998,vol. 48,p. 481 - 489
[2]Journal of the Korean Chemical Society,2013,vol. 57,p. 855 - 858
[3]Journal of the American Chemical Society,1935,vol. 57,p. 921,924

3
[ 616-45-5 ]
[ 100-39-0 ]
[ 5291-77-0 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a suspension of NaH(0.80 g, 20.0 mmol, 1.0 eq) in THF (40 mL) at 0 C was added pyrrolidone(1.70 g, 20 mmol, 1.0 eq) and the reaction mixture stirredtherein for 30 min. The reaction was then warmed to r.t. and left tostir for a further 30 min until H2 ceased to evolve. Benzyl bromide(20 mmol, 1.0 eq) was added dropwise and the reaction stirred for12 h. The reaction was quenched by the addition of H2O (500 mL)and extracted with CH2Cl2 (3 x 30 mL). The combined organicextracts were dried and concentrated in vacuo to give desiredproduct. 4.2.7.2. 1-Benzylpyrrolidin-2-one (11a) [75]. Yellow oil; 1H NMR(500 MHz, CDCl3) deltaH (ppm): 7.23-7.36 (m, 5H), 4.45 (s, 2H),3.25-3.29 (m, 2H), 2.42-2.48 (m, 2H), 1.95-2.02 (m, 2H); 13C NMR(125 MHz, CDCl3) deltaC (ppm): 175.0, 136.5, 128.6, 128.1, 127.5, 46.3,45.9, 30.9, 17.7; ESI-MS: m/z 176.1 ([M+H]+).

Reference： [1]Synthetic Communications,2009,vol. 39,p. 2297 - 2303
[2]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2011 - 2022
[3]Tetrahedron,2001,vol. 57,p. 9951 - 9957
[4]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7568 - 7573
[5]Tetrahedron,2005,vol. 61,p. 2659 - 2665
[6]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1987,vol. 41,p. 198 - 201
[7]Synthetic Communications,1995,vol. 25,p. 1265 - 1275
[8]Synthetic Communications,2007,vol. 37,p. 813 - 819
[9]Chemical Communications,2009,p. 3925 - 3927
[10]Archives of Pharmacal Research,2014,vol. 37,p. 1264 - 1270
[11]Angewandte Chemie - International Edition,2015,vol. 54,p. 11186 - 11190
Angew. Chem.,2015,vol. 127,p. 11338 - 11342,5
[12]European Journal of Medicinal Chemistry,2017,vol. 130,p. 286 - 307

4
[ 616-45-5 ]
[ 100-52-7 ]
[ 5291-77-0 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 3313 - 3314
[2]Recueil des Travaux Chimiques des Pays-Bas,1996,vol. 115,p. 231 - 238

5
[ 4383-22-6 ]
[ 201230-82-2 ]
[ 5291-77-0 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3328 - 3331

6
[ 14468-90-7 ]
[ 100-39-0 ]
[ 5291-77-0 ]

Yield	Reaction Conditions	Operation in experiment
66%	at 150 - 160℃; for 0.5h;

Reference： [1]Kramarova, E. P.; Shipov, A. G.; Orlova, N. A.; Artamkina, O. B.; Belavin, I. Yu.; Baukov, Yu. I. [Journal of general chemistry of the USSR, 1988, vol. 58, # 5, p. 970 - 979][Zhurnal Obshchei Khimii, 1988, vol. 58, # 5, p. 1093 - 1102]

7
[ 14468-90-7 ]
[ 100-44-7 ]
[ 5291-77-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	at 180 - 185℃; for 2h;

8
[ 5291-77-0 ]
[ 74-88-4 ]
[ 108303-99-7 ]

Yield	Reaction Conditions	Operation in experiment
82%		To a cold -78 C. solution of 1-benzyl-2-pyrrolidinone (0.422 g, 2.4 mmol, 1.0 equiv.) in anhydrous tetrahydrofuran (15 mL) was added lithium diisopropylamide (2.4 mL of a 2 M solution, 4.8 mmol, 2.0 equiv.) and the resultant red solution was stirred for 30 mins at -78 C., and iodomethane (0.6 mL, 9.6 mmol, 4.0 equiv.) was added. The solution was stirred at -78 C. for 1 hr and allowed to slowly warm to room temperature for 16 hrs. Saturated aqueous ammonium chloride was added and the mixture extracted with ethyl acetate. The organic fraction was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography, eluting with a gradient of 35-80% ethyl acetate in hexanes to afford the product as a tan liquid (0.374 g, 82%). 1H NMR (300 MHz, CDCl3): delta 7.37-7.34 (m, 5H), 4.52-4.41 and 4.46-4.41 (ABq, 2H, J=14.6 Hz), 3.27-3.15 (m, 2H), 2.60-2.46 (m, 1H), 2.28-2.15 (m, 1H), 1.68-1.58 (m, 1H), 1.28-1.25 (d, 3H, J=7.2 Hz).
82%		General procedure: To a cold -78 C solution of1-benzyl-2-pyrrolidinone (0.422 g, 2.4 mmol, 1.0 equiv.)in anhydrous tetrahydrofuran (15 mL) was addedlithium diisopropylamide (2.4 mL of a 2 M solution, 4.8 mmol, 2.0 equiv.)and the resultant red solution was stirred for 30 mins at -78 C,andiodomethane (0.6 mL, 9.6 mmol, 4.0 equiv.)was added. The solution was stirred at -78 C for 1 hr and allowed to slowly warm to room temperature for 16 hrs. Saturated aqueous ammonium chloride was added and the mixture extracted with ethyl acetate. The organic fraction was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentratedin vacuo.The crude product was purified by silica gel column chromatography, eluting with a gradient of 35-80% ethyl acetate in hexanes to afford the product as a tan liquid(0.374 g,82%).1H NMR (300 MHz, CDCl3): delta 7.37-7.34 (m, 5H), 4.52-4.41 and 4.46-4.41 (ABq, 2H,J= 14.6 Hz), 3.27-3.15 (m, 2H), 2.60-2.46 (m, 1H), 2.28-2.15 (m, 1H), 1.68-1.58 (m, 1H), 1.28-1.25 (d, 3H,J= 7.2 Hz).

Reference： [1]Patent: US2015/284362,2015,A1 .Location in patent: Paragraph 0293
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 293 - 297
[3]Journal of the American Chemical Society,1987,vol. 109,p. 4405 - 4407
[4]European Journal of Organic Chemistry,2014,vol. 2014,p. 129 - 139
[5]Angewandte Chemie - International Edition,2019,vol. 58,p. 4297 - 4301
Angew. Chem.,2019,vol. 131,p. 4341 - 4345,5
[6]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1987,vol. 41,p. 198 - 201

9
[ 5291-77-0 ]
[ 29897-82-3 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 3673 - 3676
[2]Synthesis,1980,p. 695 - 697
[3]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4817 - 4824
[4]Tetrahedron Letters,2006,vol. 47,p. 6173 - 6177
[5]Journal of the American Chemical Society,2009,vol. 131,p. 15032 - 15040
[6]Organic Letters,1999,vol. 1,p. 799 - 801
[7]Synlett,2010,p. 1829 - 1832
[8]Organometallics,2013,vol. 32,p. 7440 - 7444
[9]Tetrahedron Letters,1998,vol. 39,p. 1017 - 1020
[10]Journal of Organic Chemistry,2002,vol. 67,p. 4985 - 4988
[11]Journal of Organic Chemistry,2016,vol. 81,p. 3619 - 3628

10
[ 5291-77-0 ]
[ 2142-06-5 ]
[ 2399-66-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 975 - 979

11
[ 5291-77-0 ]
[ 17642-88-5 ]

Yield	Reaction Conditions	Operation in experiment
	With Lawessons reagent; In dichloromethane; at 20℃;Inert atmosphere;	General procedure: Lawesson?s reagent (2.02 g, 5.0 mmol) was added to a solution of the lactam (10 mmol) in dry CH2Cl2 (100 mL). The mixture was stirred at room temperature for 1-4 h until the starting material was consumed (TLC monitoring). The solvent was evaporated and the crude mixture was filtered on short column of silica gel (cyclohexane/EtOAc). The thiolactam (10 mmol) was suspended in dry THF (100 mL) and MeI (1.0 mL, 16 mmol) was added. The mixture was stirred at room temperature overnight. The thioiminium ion was isolated by filtration and washed with cold THF to obtain yellowish solid.

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 12318 - 12327
[2]Organic Letters,2008,vol. 10,p. 1417 - 1420
[3]Tetrahedron,2009,vol. 65,p. 2484 - 2496
[4]Synthesis,2006,p. 2327 - 2334
[5]Synthetic Communications,1990,vol. 20,p. 3085 - 3095
[6]Tetrahedron,1988,vol. 44,p. 3025
[7]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2014,vol. 120,p. 489 - 493

12
[ 26735-10-4 ]
[ 5291-77-0 ]

Reference： [1]Synthesis,1989,p. 334 - 337

13
[ 201230-82-2 ]
[ 78805-05-7 ]
[ 5291-77-0 ]
[ 4383-27-1 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 4433 - 4438

14
[ 201230-82-2 ]
[ 78805-06-8 ]
[ 5291-77-0 ]
[ 4383-27-1 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 4433 - 4438

15
[ 5291-77-0 ]
[ 31251-41-9 ]
[ 183554-46-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 673 - 686

16
[ 5291-77-0 ]
[ 141-52-6 ]
[ 89270-72-4 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 1-benzylpyrrolidin-2-one (4.63 g, 26.46 mmol) and dimethylsulfate (2.60 mL, 27.40 mmol) were heated at 80 C for 15 h under nitrogen atmosphere. The reaction mixture was then cooled at 50/60 C and a solution of sodium ethoxide (0.742 g of sodium in ethanol (14.0 mL) was added dropwise. The resulting mixture was stirred under nitrogen for 4h at 50/60C. Then nitromethane dried over CaCl2 (3 mL, 55.0 mmol), was added and the resulting solution was refluxed for 10 min. After cooling, the solvent was evaporated under reduced pressure. The residue was dissolved in CH2Cl2, filtered and the solvent evaporated in vacuo.. The resulting oil was purified by column chromatography on silica gel (CH2Cl2/AcOEt, 99/1). Further crystallization from CH2Cl2/petroleum ether afforded compound 2a as white crystals (0.424 g, 28%).

Reference： [1]European Journal of Organic Chemistry,1998,p. 1177 - 1187
[2]Journal fur Praktische Chemie (Weinheim),1999,vol. 341,p. 121 - 127
[3]Synthetic Communications,2014,vol. 44,p. 3328 - 3336

17
[ 201230-82-2 ]
[ 1026774-20-8 ]
[ 5291-77-0 ]
C₂₂H₂₄N₂O₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 5838 - 5839

18
[ 5291-77-0 ]
[ 79-20-9 ]
[ 143129-53-7 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 14193 - 14197
Angew. Chem.,2018,p. 14389 - 14393,5
[2]European Journal of Organic Chemistry,2003,p. 425 - 431
[3]Organic Letters,2017,vol. 19,p. 118 - 121

19
[ 5291-77-0 ]
[ 814-49-3 ]
[ 643754-23-8 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solutionof LDA was prepared by the addition of diisopropylamine(1.4 mL, 10 mmol, 2.0 eq) to a stirred solution of n-BuLi (1.6 M inHexanes, 6.3 mL, 10 mmol, 2.0 eq) in THF (2.5 mL) at -5 C, and theresultant solution was stirred for 30 min. A solution of 1-benzylpyrrolidin-2-one (875.5 mg, 5 mmol, 1.0 eq) in THF (5 ml) was thenadded via cannula, and the temperature rose to 15 C and the solutionstirred for 10 min. A solution of diethylchlorophosphate(0.75 mL, 5 mmol,1.0 eq) in THF (4 mL) was then added via cannula.The resulting solution was stirred at room temperature for 3 h. Thesolution was then acidified to pH 1 (1 M aqueous HCl), and theaqueous layer was separated and extracted with DCM (3 x 10 mL).The combined organic extracts were dried and concentrated invacuo to give the crude product. Purification by column chromatography(petroleum ether/AcOEt = 1/1) gave 1-benzyl-3-(diethoxyphosphinyl)-pyrrolidin-2-one as a brown oil. To a solution of 1-benzyl-3-(diethoxyphosphinyl)-pyrrolidin-2-one (311 mg,1.0 mmol,1.0 eq) in THF (5 mL)was added NaH (33 mg,1.1 mmol,1.1eq) at 0C, and the reaction mixture was stirred for 0.5 h. Then,paraformaldehyde (0.330 g, 1.1 mmol) was added at 0C and themixture was stirred for 1.5 h at room temperature. After that, brine(5 mL) was added, and the mixture was extracted with DCM(3 x 10 mL). Combined organic extracts were dried and evaporatedto give crude product which was purified by column chromatography(petroleum ether/AcOEt = 5/1).

Reference： [1]Organic Letters,2015,vol. 17,p. 952 - 955
[2]Organic Letters,2003,vol. 5,p. 4811 - 4814
[3]European Journal of Medicinal Chemistry,2017,vol. 130,p. 286 - 307

20
[ 5291-77-0 ]
[ 1885-29-6 ]
2-(1-benzyl-pyrrolidin-2-ylideneamino)benzonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1413 - 1422

21
[ 5291-77-0 ]
[ 64330-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 51.9 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.1: 87 percent / aq. hydrogen peroxide / ethyl acetate / 3.5 h / -5 °C
	Multi-step reaction with 2 steps 1: 1.) LDA / 1.) THF, hexane, from -78 to -20 deg C, 30 min, 2.) THF, hexane, -78 deg C, 10 min 2: 83 percent / 30percent aq. H₂O₂ / ethyl acetate / 0.5 h / 15 - 20 °C

Reference： [1]Mun, JiYoung; Smith, Michael B. [Synthetic Communications, 2007, vol. 37, # 5, p. 813 - 819]
[2]Li; Smith [Synthetic Communications, 1995, vol. 25, # 8, p. 1265 - 1275]

22
[ 23583-21-3 ]
[ 5291-77-0 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1986,vol. 51,p. 2034 - 2049
[2]Nippon Kagaku Zasshi,1956,vol. 77,p. 599,601
Chem.Abstr.,1958,p. 9070

23
[ 5291-77-0 ]
[ 1559-02-0 ]
1-[(1-benzyl-2-oxo-pyrrolidin-3-ylidene)hydroxymethyl]cyclopropanecarboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 0℃; for 1.75h;	LDA (1M, 13ML) was stirred in THF (25mL) at-78 C, then 1-benzyl- pyrrolidine (2. 0g, in solution of THF, 3mL) was added. After stirring for 30 minutes, cyclopropane-1, 1-dicarboxylic acid diethyl ester (2.80g, in solution of THF, 3mL) was added. The reaction was stirred at-78 C for another 15 minutes, then at 0 C for lhour. The reaction mixture was quenched with saturated NH4C1, diluted with EtOAc, then washed with water and brine. The organic layer was dried over MgSO4, filtered and the filtrate was concentrated at reduced pressure. The resulting residue was purified via flash column chromatography (Hexanes/EtOAc gradient) to afford the title compound (2. 0g, 55%). MS (APCI+): 772/Z 316 (M+H) +

Reference： [1]Patent: WO2005/26165,2005,A1 .Location in patent: Page/Page column 71; 140-141

24
[ 5291-77-0 ]
[ 1559-02-0 ]
1-[(1-benzyl-2-oxo-pyrrolidin-3-ylidene)-hydroxy-methyl]-cyclopropanecarboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%		LDA (1M, 13ML) was stirred in THE (25ML) AT-78 C, then 1-benzyl- pyrrolidine (2. 0g, in solution of THF, 3ML) was added. After stirring for 30 minutes, cyclopropane-1, 1-DICARBOXYLIC acid diethyl ester (2.80g, in solution of THF, 3mL) was added. The reaction was stirred at-78 C for another 15 minutes, then at 0 C for lhour. The reaction mixture was quenched with saturated NH4CI, diluted with EtOAc, then washed with water and brine. The organic layer was dried over MGS04, filtered and the filtrate was concentrated at reduced pressure. The resulting residue was purified via flash column chromatography (Hexanes/EtOAc gradient) to afford the title compound (2. 0g, 55%). MS (APCI+) : NEZ 316 (M+H) +.

Reference： [1]Patent: WO2005/26154,2005,A1 .Location in patent: Page/Page column 113-114

25
[ 5291-77-0 ]
[ 1044659-29-1 ]
1-benzyl-3-[1-(tert-butyl-dimethyl-silanyloxy)-cyclopropyl]-hydroxy-methylene}-pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%		LDA (2M, 14mL) was stirred in THF (SOmL) AT-78 OC, then 1-BENZYL-2- pyrrolidinone (4.04g) was added slowly as solution in THF (5mL). After 30 minutes, crude 1- (TERT-BUTYL-DIMETHYL-SILANYLOXY)-CYCLOPROPANECARBOXYLIC acid ethyl ester was added as a solution in THF (5mL). The reaction mixture remained at-78 C for 30 minutes, and then was warmed to 0 C. After 1 hour, saturated NH4CI was added to quench excess base, then the reaction mixture was diluted with EtOAc and washed with saturated NaHC03, water, and brine. The organic layer was dried over MgS04, filtered, and the filtrate was concentrated. The resulting residue was purified via flash column chromatography (Hexanes/EtOAc gradient) to afford the title compound (3.23g, 38%). MS (APCI+): m/z 374 (M+H) +.
38%		LDA (2M, 14ML) was stirred in THF (50ML) at-78 C, then l-benzyl-2- pyrrolidinone (4.04g) was added slowly as solution in THF (5ML). After 30 minutes, crude 1- (TERT-BUTYL-DIMETHYL-SILANYLOXY)-CYCLOPROPANECARBOXYLIC acid ethyl ester was added as a solution in THF (SML). The reaction mixture remained at-78 C for 30 minutes, and then was warmed to 0 C. After 1 hour, saturated N144CI was added to quench excess base, then the reaction mixture was diluted with EtOAc and washed with saturated NAHC03, water, and brine. The organic layer was dried over MGS04, filtered, and the filtrate was concentrated. The resulting residue was purified via flash column chromatography (Hexanes/EtOAc gradient) to afford the title compound (3.23g, 38%). MS (APCI+): M/Z 374 (M+H) +

Reference： [1]Patent: WO2005/26154,2005,A1 .Location in patent: Page/Page column 120
[2]Patent: WO2005/26165,2005,A1 .Location in patent: Page/Page column 70; 73; 147

26
[ 5291-77-0 ]
[ 39263-32-6 ]
[ 303096-59-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide;Zinc chloride; In chloroform, phosphorous oxychloride; ethanol; nitrobenzene;	Synthesis Example 1 1-Benzyl-6-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine N-Benzylpyrrolidone (1.8 g, 10.4 mmol) was dissolved in 4 ml of chloroform, phosphorous oxychloride (1.8 g, 11.7 mmol) was added thereto, and the mixture was stirred at room temperature for 30 minutes. 4-Bromo-2-cyanoaniline (2.0 g, 10 mmol) was added thereto and the mixture was refluxed by heating. The reaction mixture was poured on ice water, and neutralized with 20% sodium hydroxide aqueous solution. After extraction by chloroform, the organic layer was dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was dissolved in 100 ml of nitrobenzene, 2 g of zinc chloride was added and the mixture was heated at 160 C. for 3 hours. 20% sodium hydroxide aqueous solution was added to the reaction solution, and it was extracted with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, it was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (silica gel 50 g, ethyl acetate/hexane=1/2). The objective fraction was concentrated under reduced pressure, ethanol was added to the residue, and a precipitate was collected by filtration. The precipitate was washed with ethanol, and then dried under reduced pressure to obtain the title compound (1.2 g, 3.4 mmol). 1H-NMR (DMSO-d6) delta: 2.86 (2H, t, J=8.0 Hz), 3.41 (2H, t, J=8.0 Hz), 4.59 (2H, s), 7.24-7.33 (6H, m), 7.42 (1H, dd, J=9.2, 2.2 Hz), 8.12 (1H, d, J=2.2 Hz). Mass (ESI+); 354 (M+H), 356
	With sodium hydroxide;Zinc chloride; trichlorophosphate; In ethanol; chloroform; nitrobenzene;	Reference Example 1 1-Benzyl-6-bromo-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine N-Benzylpyrrolidone (1.8 g, 10.4 mmol) was dissolved in chloroform (4 ml) and stirred at room temperature for 30 minutes in the presence of phosphorus oxychloride (1.8 g, 11.7 mmol). 4-Bromo-2-cyanoaniline (2.0 g, 10 mmol) was added, followed by heating at reflux for 3 hours. The reaction mixture was poured into ice-cold water and neutralized with 20% aqueous sodium hydroxide. After extraction with chloroform, the organic layer was dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was dissolved in nitrobenzene (10 ml)and heated at 160C for 3 hours in the presence of zinc chloride (2 g). Aqueous sodium hydroxide (20%) was added to the reaction mixture, which was then extracted with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, the residue was applied to silica gel column chromatography (silica gel 50 g, ethyl acetate/hexane = 1/2). Fractions of interest were concentrated under reduced pressure and ethanol was added to the residue to collect a precipitated product by filtration. The precipitated product was washed with ethanol and dried under reduced pressure to give the titled compound (1.2 g, 3.4 mmol).1H-NMR (DMSO-d6) delta: 2.86 (2H, t, J=8.0Hz), 3.41 (2H, t, J=8.0Hz), 4.59 (2H, s), 7.24-7.33 (6H, m), 7.42 (1H, dd, J=9.2, 2.2Hz), 8.12 (1H, d, J=2.2Hz). Mass (ESI+); 354 (M+H), 356

Reference： [1]Patent: US2003/207863,2003,A1
[2]Patent: EP1308513,2003,A1

27
[ 5291-77-0 ]
[ 61272-77-3 ]
5-fluoro-2-{(1-benzyl-2-pyrrolidinylidene) amino} benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; trichlorophosphate; In ice-water; chloroform;	Synthesis Example 13 1-benzyl-6-fluoro-2,3-dihydro-1H-pyrrolo [2,3-b] quinoline-4-ylamine hydrochloride Phosphorus oxychloride (0.51 ml) was added to a solution of 1-benzyl-2-pyrrolidone (0.84 ml) in chloroform (3 ml). The solution was stirred at room temperature for 30 minutes, and <strong>[61272-77-3]2-amino-5-fluorobenzonitrile</strong> (0.65 ml) was added thereto. The reaction mixture was refluxed for 3 hours while heating and then ice-water was added thereto. Further, the mixture was neutralized by adding 20% aqueous sodium hydroxide solution and extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give 5-fluoro-2-{(1-benzyl-2-pyrrolidinylidene) amino} benzonitrile (1.68 g).

Reference： [1]Patent: US2003/139442,2003,A1

28
[ 5291-77-0 ]
[ 245546-81-0 ]

Yield	Reaction Conditions	Operation in experiment
68%	With ammonium nitrate; In sulfuric acid;	(b) N-(3-nitro-benzyl)-2-pyrrolidinone (~20%) Prepared analogously to Example D by reacting N-benzyl-2-pyrrolidinone with ammonium nitrate in concentrated sulphuric acid and subsequent crystallisation from petroleum ether/ether. Yield: 68% of theory; Melting point: 55-75 C.

Reference： [1]Patent: US6043254,2000,A

29
[ 5291-77-0 ]
[ 61272-77-3 ]
5-fluoro-2-{(1-benzyl-2-pyrrolidinylidene)amino}benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In chloroform; water;	Reference Example 13 1-Benzyl-6-fluoro-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine hydrochloride To a solution of 1-benzyl-2-pyrrolidone (0.84 ml) in chloroform (3 ml), phosphorus oxychloride (0.51 ml) was added and stirred at room temperature for 30 minutes, followed by addition of <strong>[61272-77-3]2-amino-5-fluorobenzonitrile</strong> (0.65 ml). After heating at reflux for 3 hours, ice-cold water was added to the reaction mixture. Further, the reaction mixture was neutralized with 20% aqueous sodium hydroxide and extracted with chloroform. The extracted solution was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give 5-fluoro-2-{(1-benzyl-2-pyrrolidinylidene)amino}benzonitrile (1.68 g).

Reference： [1]Patent: EP1308513,2003,A1

30
[ 5291-77-0 ]
[ 24424-99-5 ]
N⁽¹⁾-benzyl-2-pyrrolidone-3-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hexamethyldisilazane; In tetrahydrofuran; at -40℃;	General procedure: Benzylbutyrolactam (3) available commercially as a starting material according to the method of Reaction Scheme 1 above to give compound (4)This was substituted with benzyl bromide (RX) to obtain LTC-2. (Total yield: 72.7%).

Reference： [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 3313 - 3318
[2]Chemical Communications,2009,p. 3925 - 3927
[3]Archives of Pharmacal Research,2014,vol. 37,p. 1264 - 1270
[4]Patent: KR101497962,2015,B1 .Location in patent: Paragraph 0064; 00139; 0140

31
[ 5291-77-0 ]
[ 848414-09-5 ]
1-benzyl-3-[hydroxy-(5-methanesulfonyl-furan-2-yl)-methylene]-pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		LDA was stirred in THF (50mL) AT-78 C, then L-BENZYL-2-PYRROLIDINONE (in solution of THF, 5mL) was added dropwise over 2 minutes. After 45 minutes, 5-Methanesulfonyl-furan-2-carboxylic acid ethyl ester (in solution of THF, 3mL) was added dropwise over 5 minutes. After additional 15 minutes at-78 C, reaction was warmed to room temperature. After 90 minutes, the reaction mixture was diluted with EtOAc and washed with saturated NH4CI, H20, and brine. Organic layer was dried over MGS04, filtered and filtrate concentrated. Resulting residue was purified via flash column chromatography (Hexanes/EtOAc gradient) to afford the title compound (5.02g, 87%). MS (APCI+): M/Z 348 (M+H) +.

Reference： [1]Patent: WO2005/26154,2005,A1 .Location in patent: Page/Page column 116-117

32
[ 5291-77-0 ]
[ 848414-09-5 ]
1-benzyl-3-[hydroxy-(5-methanesulfonylfuran-2-yl)methylene]pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		LDA was stirred in THF (50mL) AT-78 C, then 1-benzyl-2-pyrrolidinone (in solution of THF, 5mL) was added dropwise over 2 minutes. After 45 minutes, 5-Methanesulfonyl-furan-2-carboxylic acid ethyl ester (in solution of THF, 3mL) was added dropwise over 5 minutes. After additional 15 minutes AT-78 C, reaction was warmed to room temperature. After 90 minutes, the reaction mixture was diluted with EtOAc and washed with saturated NH4CL, H20, and brine. Organic layer was dried over MGS04, filtered and filtrate concentrated. Resulting residue was purified via flash column chromatography (Hexanes/EtOAc gradient) to afford the title compound (5.02g, 87%). MS (APCI+): 7N/Z 348 (M+H) +.

Reference： [1]Patent: WO2005/26165,2005,A1 .Location in patent: Page/Page column 72; 143-144

33
[ 5291-77-0 ]
[ 79-22-1 ]
[ 71725-74-1 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8205 - 8210
[2]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 282 - 291

34
[ 5291-77-0 ]
[ 108-64-5 ]
(rac)-1-benzyl-3-(3-methylbutanoyl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78.7%		(S)-1-Benzyl-3-(3-methylbutanoyl)pyrrolidin-2-one Charge a 5 L, 3-neck round bottom flask equipped with a magnetic stirrer, thermal couple, addition funnel and N2 inlet with diisopropylamine (176 mL, 1265 mmoles) and 2-methyltetrahydrofuran (500 mL). Cool the solution to ~-10 C. (salt/ice bath) with stirring and add a solution of n-BuLi (2.5 M in hexanes, 504 mL, 1259 mmoles) drop wise while maintaining a temperature at or below 0 C. Rinse the addition funnel with 2-methyltetrahydrofuran (25 mL). Stir the solution for about 15 min, at ~-5 C. Add a solution of N-benzyl-2-pyrrolidinone (100.8 g, 575 2 mmoles), ethyl isovalerate (90 g, 690 mmoles) in 2-Me-THF (500 mL) drop wise at a rate to maintain a temperature at or below 5 C. to provide a yellow slurry. Stir the reaction mixture about 1 hour at -5 C., add heptane (1 L) drop wise, and stir for an additional 1 hr. at -5 C. Collect the solid by filtration through a medium fritted funnel, wash with a 1:1 solution of 2-methyltetrahydrofuran/heptane (250 mL) followed by heptane (250 mL) and air dry until the solid becomes powder-like. Place the yellow solid into a 5 L, 3-neck round bottom flask equipped with a magnetic stirrer and add MTBE (1 L) and 10% citric acid (1 L). Stir the mixture for about 1 hour at room temperature to provide a homogeneous mixture. Separate the layers and wash the organic layer with H2O (2*500 mL), followed by brine (500 mL). Dry over Na2SO4, filter and concentrate to give the crude intermediate (128 g) as an orange oil. A Kuegelrohr distillation removes the major impurity from the crude material to yield the desired intermediate as a dark orange oil (117.4 g, 452.7 mmoles, 78.7% yield). 1H NMR (300 MHz, CDCl3) delta 7.38-7.16 (m, 5H), 4.55-4.35 (m, 2H), 3.62 (dd, 1H, J=5.86, 9.37 Hz), 3.38-3.14 (m, 2H), 2.92-2.8 (m, 1H), 2.64-2.42 (m, 2H), 2.28-2.11 (m, 1H), 2.08-1.93 (m, 1H), 0.96 (d, 3H, J=7.03 Hz) 0.93 (d, 3H, J=7.04 Hz). GC/MS=260 (M+1).

Reference： [1]Patent: US2010/261762,2010,A1 .Location in patent: Page/Page column 19
[2]Organic Letters,2016,vol. 18,p. 4978 - 4981

35
[ 693-03-8 ]
[ 5291-77-0 ]
[ 29897-82-3 ]
[ 1260380-74-2 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 12792 - 12796

36
[ 5291-77-0 ]
[ 925-90-6 ]
[ 29897-82-3 ]
[ 1260380-69-5 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 12792 - 12796
[2]Journal of Organic Chemistry,2013,vol. 78,p. 8305 - 8311

37
[ 5291-77-0 ]
[ 1589-82-8 ]
[ 29897-82-3 ]
1,2-dibenzylpyrrolidine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 12792 - 12796

38
[ 5291-77-0 ]
[ 100-58-3 ]
[ 29897-82-3 ]
[ 1025-56-5 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 12792 - 12796

39
[ 534616-88-1 ]
[ 5291-77-0 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 5708 - 5711

40
[ 18085-37-5 ]
[ 5291-77-0 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 5708 - 5711

41
[ 1307661-09-1 ]
[ 5291-77-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tetrakis(trifluoroacetato)rhodium(II); water; In toluene; for 10h;Reflux; Inert atmosphere;	A mixture of bis[(4-chlorophenyl)methyl](4-chloro-3-butynyl)amine (5) (31.8 mg, 0.090 mmol) and rhodium trifluoroacetate dimer (Rh2(tfa)4, 11.8 mg, 0.018 mmol) in toluene (1.0 mL) and water (0.01 mL) was heated at reflux for 10 h under argon. After being cooled to room temperature, the mixture was filtered through a short pad of Celite with the aid of ethyl acetate. The combined filtrates were concentrated to give a crude oil, which was chromatographed on silica gel (hexane-ethyl acetate) to afford the title compound (15.5 mg, 82%) as an oil. 1H NMR delta 2.01 (quintet, J = 7.7 Hz, 2H), 2.45 (t, J = 7.7 Hz, 2H), 3.26 (t, J = 7.7 Hz, 2H), 4.42 (s, 2H), 7.18 (d, J = 8.4 Hz, 2H), 7.30 (d, J = 8.4 Hz, 2H). 13C NMR delta 17.78, 30.81, 46.02, 46.60, 128.87 (2 carbons), 129.51 (2 carbons), 133.51, 135.22, 174.97. IR (neat) 3060, 3049, 2926, 1682 (CO), 1493, 1093, 1016, 802 cm-1.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2458 - 2461

42
[ 5291-77-0 ]
benzyl(halo)magnesium [ No CAS ]
[ 29897-82-3 ]
1,2-dibenzylpyrrolidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 8305 - 8311

43
[ 5291-77-0 ]
halo(butyl)magnesium [ No CAS ]
[ 29897-82-3 ]
[ 1260380-74-2 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 8305 - 8311

44
[ 5291-77-0 ]
halo(phenyl)magnesium [ No CAS ]
[ 29897-82-3 ]
[ 1025-56-5 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 8305 - 8311

45
[ 5291-77-0 ]
[ 75-16-1 ]
[ 96567-93-0 ]

Yield	Reaction Conditions	Operation in experiment
58.1%	In tetrahydrofuran; at -20℃; for 3h;	(1) Preparation of 1-benzyl-3-methylpyrrolidin-3-ol 1-benzylpyrrolidone (1.1g, 6.3mmol) was dissolved in 4mL THF under stirring at -20C. The resulting solution was dropwisely added to a solution of methyl magnesium bromide (13.2mL, 12.2mmol) in THF. The stirring was continued for 3 hours. After the completion of reaction, the reaction solution was dropwisely added to an ice water. The resulting mixture was washed with a saturated aqueous NaCl solution, dried over Na2SO4, and purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate = 20:1 (volumetric ratio)) to produce the product of 1-benzyl-3-methylpyrrolidinyl-3-ol (0.7g) in a yield of 58.1%.

Reference： [1]Patent: EP2703398,2014,A1 .Location in patent: Paragraph 0063; 0064

46
[ 5291-77-0 ]
[ 1191-95-3 ]
1-benzyl-3-(1-hydroxycyclobutyl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%		To a cold (-78 C.) solution of 1-benzyl-2-pyrrolidinone (1.0 g, 5.7 mmol, 1.0 equiv.) in anhydrous tetrahydrofuran (19 mL) was added lithium diisopropylamide (3.15 mL of a 2 M solution in tetrahydrofuran, 1.1 eq.) and the mixture stirred for 1 hr at -78 C. Cyclobutanone (0.426 mL, 5.7 mmol, 1.0 equiv.) and boron trifluoride diethyl etherate (0.704 mL, 5.7 mmol, 1.0 equiv.) were added and the reaction mixture stirred at -78 C. for 4 hrs. The reaction was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic fraction was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting from silica gel with a gradient of 50-100% ethyl acetate in hexanes to give a white solid (0.714 g, 51%). 1H NMR (300 MHz, CDCl3): delta 7.36-7.20 (m, 5H), 4.56-4.51 and 4.42-4.37 (AB, 2H, J=14.7 Hz), 4.24 (s, 1H), 3.28-3.21 (m, 2H), 2.78-2.72 (t, 1H, J=2.7 Hz), 2.34-1.89 (m, 7H), 1.66-1.52 (m, 1H); ESI (m/z): 246.0 (M+H).

Reference： [1]Patent: US2015/284362,2015,A1 .Location in patent: Paragraph 0301

47
[ 41194-02-9 ]
[ 5291-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 1% Pd on activated carbon; hydrogen; In toluene; at 50℃; under 15201 Torr; for 2h;	General procedure: A glass ampule for hydrogenolysis (preliminary evacuated and refilled with argon) was charged with a 1% Pd/Sibunit (25 mg, 2.35*10-3 mg-atom of Pd) and substrate 1 (0.23 mmol). The ampule was again evacuated and refilled with argon. After adding the solvent (2 mL), the ampule was transferred into filled with argon stainless steel autoclave (50 cm3). The autoclave was flushed with purified hydrogen and the hydrogen pressure was adjusted to 20 atm. Then, the reaction mixture was magnetically stirred at temperature indicated in Table 1. After completion of the experiment, the reaction mixture was filtered through a silica gel pad (1.5 cm thick) to remove the catalyst, the products were eluted with ethyl acetate. After removal of the solvent in vacuo, the residue was subjected to NMR spectroscopy, mass spectrometry, and elemental analyses.

Reference： [1]Russian Chemical Bulletin,2015,vol. 64,p. 859 - 863
Izv. Akad. Nauk, Ser. Khim.,2015,p. 859 - 863,5

48
[ 5291-77-0 ]
[ 7051-34-5 ]
1-benzyl-3-(cyclopropylmethyl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		1-Benzylpyrrolidin-2-one (5.0 g, 28.6 mmol) was dissolved in THF (100 mL) and cooled to -78 C. n-BuLi (2.5M, 13.7 mL, 34.3 mmol) was added dropwise at -78 C. and the reaction mixture was stirred at -78 C. for 30 minutes. (Bromo-methyl)cyclopropane (4.6 g, 34.3 mmol) was added and stirring continued at -78 C. for 30 minutes. The reaction mixture was allowed to reach RT slowly overnight. The mixture was quenched with sat. aq. NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptanes/EtOAc 2:1) affording 1-benzyl-3-(cyclopropylmethyl)-pyrrolidin-2-one (3.9 g, 60%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): 0.05 (m, 2H); 0.43 (m, 2H); 0.74 (m, 1H); 1.22 (m, 1H); 1.68 (m, 1H); 1.76 (m, 1H); 2.21 (m, 1H); 2.55 (m, 1H); 3.08 (m, 2H); 4.43 (q, 2H); 7.24 (m, 5H).

Reference： [1]Patent: US2016/95858,2016,A1 .Location in patent: Paragraph 5569; 5570

49
[ 5291-77-0 ]
[ 5340-78-3 ]
1-benzyl-3-(3,3-dimethylbutanoyl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With lithium diisopropyl amide In 2-methyltetrahydrofuran; hexane at -10 - 5℃; for 0.75h;

Reference： [1]Lynch, Denis; Deasy, Rebecca E.; Clarke, Leslie-Ann; Slattery, Catherine N.; Khandavilli, U. B. Rao; Lawrence, Simon E.; Maguire, Anita R.; Magnus, Nicholas A.; Moynihan, Humphrey A. [Organic Letters, 2016, vol. 18, # 19, p. 4978 - 4981]

50
[ 5291-77-0 ]
[ 2868-37-3 ]
1-benzyl-3-(cyclopropanecarbonyl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 1-benzyl-2-pyrrolidone With lithium diisopropyl amide In tetrahydrofuran; hexane at -75 - -60℃; for 1.16667h; Stage #2: methyl cyclopropylcarboxylate In tetrahydrofuran; hexane at -75 - -60℃; for 1.33333h;

51
[ 4630-82-4 ]
[ 5291-77-0 ]
(rac)-1-benzyl-3-(cyclohexanecarbonyl)pyrrolidin-2-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 14193 - 14197
Angew. Chem.,2018,p. 14389 - 14393,5
[2]Organic Letters,2017,vol. 19,p. 118 - 121
[3]Organic Letters,2016,vol. 18,p. 4978 - 4981

52
[ 93-58-3 ]
[ 5291-77-0 ]
(rac)-3-benzoyl-1-benzylpyrrolidin-2-one [ No CAS ]

53
[ 5291-77-0 ]
[ 101-41-7 ]
(rac)-1-benzyl-3-(2-phenylacetyl)pyrrolidin-2-one [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 4978 - 4981
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 14193 - 14197
Angew. Chem.,2018,p. 14389 - 14393,5
[3]Organic Letters,2017,vol. 19,p. 118 - 121

54
[ 29897-82-3 ]
[ 5291-77-0 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 870 - 873

55
[ 5291-77-0 ]
[ 100-52-7 ]
[ 66075-39-6 ]

Yield	Reaction Conditions	Operation in experiment
60%		1-benzyl-pyrrolidinone (1b) 121mg, 0.69mmol) was dissolved in dichloromethane (6mL) solvent, was added trifluoromethanesulfonic anhydride (0.23 mL, 1.4 mmol) at -78 deg.] C under argon, - 78 stirred for 45min, added dropwise benzaldehyde (0.20mL, 2.0mmol), - 78 deg.] C was stirred for 5min raised to 0 , dropwise addition of triethylamine (0.20mL, 1.4mmol), stirred at rt for 1h. Was added 10mL of (1N) hydrochloric acid, reaction was quenched after quenched, allowed to separate, and the aqueous phase was extracted with dichloromethane (3 × 20mL). The combined organic phases were washed with saturated sodium bicarbonate solution (30mL) and brine (20mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 1-benzyl-3-benzyloxy-vinylpyrrolidone after purification ( referred to as compound 2b), the resulting compound 2b as a colorless liquid (109mg, 60%).

Reference： [1]Patent: CN106748949,2017,A .Location in patent: Paragraph 0022; 0023

56
[ 4630-82-4 ]
[ 5291-77-0 ]
(S)-1-benzyl-3-((R)-cyclohexyl(hydroxy)methyl)pyrrolidin-2-one [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 118 - 121

57
[ 5291-77-0 ]
[ 556-24-1 ]
(rac)-1-benzyl-3-(3-methylbutanoyl)pyrrolidin-2-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 14193 - 14197
Angew. Chem.,2018,p. 14389 - 14393,5
[2]Organic Letters,2017,vol. 19,p. 118 - 121

58
[ 5291-77-0 ]
[ 124-38-9 ]
[ 109859-99-6 ]

Yield	Reaction Conditions	Operation in experiment
56%		Into a -20C solution of i-.benzylpyrroiidin-2-.one (1.00 g, 571 mmoi, 1.00 eq.) in THF (20 mL) underN2 was added lithium diisopropylamide (LDA) (6.3 mE, 2.0 M in TEIF, 12.6 mmoi, 220 eq.) dropwise over 5 mm. The resulting mixture was allowed to stir at -20C under N2 for 1.5 h. Dry carbon dioxide gas was run through this solution at -20 0 for 0.5 h. The reaction was then quenchedby saturated aqueous NH4CI solution (6.3 mL) and then diluted with water. The pH was adjusted to2-3 with concentrated HC1. The resulting solution was extracted with EtOAc thrice. The combined organic layers were dried over anhydrous sodium sulfate. The solids were filtered off. The filtrate was concentrated under reduced pressure to provide I -benzyi-2-oxopyrroiidine-3-carboxyiic acid as a colorless oil (700 rng, 56%). LCMS (ES) [M-f-1] m/z 220.2.

Reference： [1]Patent: WO2018/119208,2018,A1 .Location in patent: Page/Page column 92

59
[ 2905-56-8 ]
[ 5291-77-0 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 8867 - 8871
Angew. Chem.,2019,vol. 131,p. 8959 - 8963,5

60
[ 5291-77-0 ]
[ 18595-16-9 ]
methyl 2-((1-benzylpyrrolidin-3-ylidene)amino)-5-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%		A solution of 1-benzylpyrrolidin-2-one (6.30 g, 35.9 mmol) in methylene chloride (200 ml_) was treated with phosphorous oxychloride (4.50 ml_, 49.2 mmol) and stirred under a nitrogen atmosphere at ambient temperature for 4 h. The mixture was treated with a solution of methyl 2-amino-5-methylbenzoate (5.30 g, 32.1 mmol) in methylene chloride (20 ml_) and heated at reflux for 48 h. After this time, the reaction mixture was allowed to cool to ambient temperature and concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate and then water. The organic layer was extracted with 0.4 M hydrochloric acid, and the aqueous extract was basified to pH ~12 by adding sodium hydroxide. The mixture was extracted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide methyl 2-((1-benzylpyrrolidin-3-ylidene)amino)-5-methylbenzoate (8.40 g, 81 %) as a pale yellow oil: ESI MS m/z 323 [C20H22N2O2 + H]+.

Reference： [1]Patent: WO2019/241469,2019,A1 .Location in patent: Page/Page column 69-70

61
[ 4897-84-1 ]
[ 100-46-9 ]
[ 5291-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	With iron(III) chloride; In neat (no solvent); at 80℃; for 1.5h;Sealed tube;	General procedure: An oven-dried pressuretube equipped with a magnetic stirrer was evacuated with nitrogen. To this was added of ester 1a(492 uL, 5.04 mmol), followed by amine 2a (0.5 mL, 4.58 mmol), and finally FeCl3 (111 mg, 0.684 mmol).The mixture was then sealed and stirred at 80 C (0.5 mL of CH3CN was added if the reaction mixturesolidified). The reaction was monitored by TLC until completion upon which it was diluted withEtOAc and washed once with saturated NaHCO3 and once with distilled H2O. The combined aqueouslayers were extracted once with ethyl acetate. The combined organic layers were then dried overMgSO4, filtered and solvents removed under reduced pressure. The crude product was purified bysilica gel flash column chromatography using a combination of hexane and ethyl acetate (3:2).

Reference： [1]Molecules,2020,vol. 25

62
[ 105-54-4 ]
[ 100-46-9 ]
[ 5291-77-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	With iron(III) chloride; In neat (no solvent); at 80℃;Sealed tube;	General procedure: An oven-dried pressuretube equipped with a magnetic stirrer was evacuated with nitrogen. To this was added of ester 1a(492 uL, 5.04 mmol), followed by amine 2a (0.5 mL, 4.58 mmol), and finally FeCl3 (111 mg, 0.684 mmol).The mixture was then sealed and stirred at 80 C (0.5 mL of CH3CN was added if the reaction mixturesolidified). The reaction was monitored by TLC until completion upon which it was diluted withEtOAc and washed once with saturated NaHCO3 and once with distilled H2O. The combined aqueouslayers were extracted once with ethyl acetate. The combined organic layers were then dried overMgSO4, filtered and solvents removed under reduced pressure. The crude product was purified bysilica gel ash column chromatography using a combination of hexane and ethyl acetate (3:2).

Reference： [1]Molecules,2020,vol. 25

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
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P243	Take precautionary measures against static discharge.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P312	Call a POISON CENTER or doctor/physician if you feel unwell.
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P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 5291-77-0 ] {[proInfo.proName]}

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Application In Synthesis of [ 5291-77-0 ]

[ 5291-77-0 ] Synthesis Path-Downstream 1~62

Related Functional Groups of [ 5291-77-0 ]

Aryls

Amides

Related Parent Nucleus of [ 5291-77-0 ]

Pyrrolidines

Precautionary Statements-General

Prevention

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Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 5291-77-0 ]

Related Parent Nucleus of
[ 5291-77-0 ]