[ CAS No. 5747-92-2 ] {[proInfo.proName]}

Name: 5747-92-2|Ethyl 1-benzylpyrrolidine-3-carboxylate|97%
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SKU: A754288
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Quality Control of [ 5747-92-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 5747-92-2 ]

Product Details of [ 5747-92-2 ]

CAS No. :	5747-92-2	MDL No. :	MFCD04039852
Formula :	C₁₄H₁₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CYPXEPWPTXKUPL-UHFFFAOYSA-N
M.W :	233.31	Pubchem ID :	11622765
Synonyms :

Calculated chemistry of [ 5747-92-2 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	71.04
TPSA :	29.54 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.93
Log Po/w (XLOGP3) :	2.11
Log Po/w (WLOGP) :	1.54
Log Po/w (MLOGP) :	2.12
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	2.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.55
Solubility :	0.662 mg/ml ; 0.00284 mol/l
Class :	Soluble
Log S (Ali) :	-2.36
Solubility :	1.02 mg/ml ; 0.00435 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.5
Solubility :	0.0729 mg/ml ; 0.000313 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.28

Safety of [ 5747-92-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H317-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5747-92-2 ]

* 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.

Upstream synthesis route of [ 5747-92-2 ]
Downstream synthetic route of [ 5747-92-2 ]

[ 5747-92-2 ] Synthesis Path-Upstream 1~15

1
[ 5747-92-2 ]
[ 72925-15-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In ethanol for 6 h;	A solution of1-benzyl-pyrrolidine-3-carboxylic acid ethyl ester (10.00 g, 42.9 mmol) in ethanol (200 mL) was hydrogenated in the presence of 10percent Pd/C (2.0 g) at 60 psi for 6 hours. The resulting suspension was filtered through celite, washed withCH2C12, and concentrated under reduced pressure to leave the crude <Desc/Clms Page number 130>title compound(7. 12 g, 100percentyield). 1H NMRa(CDC13) 4.16 (q, 2H),3. 02- 3.17 (m, 3H), 2.82-2. 94 (m, 2H), 1.91-2. 07 (m, 2H), 1.26 (t, 3H). LCMS(APCI+) 144 (100percent, MH+).
100%	With hydrogen In ethanol for 6 h;	A solution of1-benzyl-pyrrolidine-3-carboxylic acid ethyl ester (10.00g, 42.9 mmol) in ethanol (200 mL) was hydrogenated in the presence of 10percentPd/C (2.0 g) at 60 psi for 6 hours. The resulting suspension was filtered through celite, washed withCH2Cl2, and concentrated under reduced pressure to leave the crude <Desc/Clms Page number 158>title compound (7.12 g, 100percentyield). 1H NMRO(CDCl3) 4.16 (q,2H), 3.02- 3.17(m, 3H), 2.82-2. 94 (m, 2H), 1.91-2. 07 (m, 2H), 1.26 (t, 3H). LCMS(APCI+) 144 (100percent,Moi+).
99%	With hydrogen In ethanol at 60℃; for 16 h;	Palladium hydroxide on carbon (10percent by weight, 32 g) was added to a solution of 1-benzyl-pyrrolidine-3-carboxylic acid ethyl ester (320 g, 1.37 mol) in ethanol (3000 mL) and hydrogenated (40 psi, 60° C.) for 16 hours. The reaction mixture was filtered through Arbocel.(TM). then the filtrate was concentrated under reduced pressure to afford the title compound as a brown oil (195 g, 99percent). ¹H NMR (400 MHz, CDCl₃) δ: 1.23 (t, 3H), 1.90-2.00 (m, 2H), 2.79-2.88 (m, 2H) 3.00-3.12 (m, 3H), 4.10 (q, 2H)

Reference： [1] Patent: WO2005/49602, 2005, A1, . Location in patent: Page/Page column 89; 90; 129; 130
[2] Patent: WO2005/49605, 2005, A1, . Location in patent: Page/Page column 117; 118; 157; 158
[3] Patent: US2010/120793, 2010, A1, . Location in patent: Page/Page column 36
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 233 - 241
[5] Patent: US5686463, 1997, A,
[6] Patent: WO2003/103669, 2003, A1, . Location in patent: Page 71-72

2
[ 93102-05-7 ]
[ 140-88-5 ]
[ 5747-92-2 ]

Reference： [1] Synthesis, 2006, # 16, p. 2646 - 2648
[2] Tetrahedron Letters, 2010, vol. 51, # 7, p. 1026 - 1029
[3] Chemistry Letters, 1984, p. 1117 - 1120

3
[ 64-17-5 ]
[ 10603-52-8 ]
[ 5747-92-2 ]

Yield	Reaction Conditions	Operation in experiment
58%	With hydrogenchloride In 1,4-dioxane	A solution of 159B (1.5g, 7.9 [MMOL)] in [ETOH] (40 ml) was treated with 4M [HCI-] dioxane (20 ml) and stirred overnight. The reaction mixture was cooled to [0 °C,] treated with saturated aqueous [NAHC03] until neutralized, and extracted with EtOAc. The organic layer was dried over [NA2SO4] and concentrated. Flash chromatography (35-50percent EtOAc/hexane) provided 159C (1.1 g, 58percent).

Reference： [1] Patent: WO2003/103669, 2003, A1, . Location in patent: Page 71-72

4
[ 93102-06-8 ]
[ 140-88-5 ]
[ 5747-92-2 ]

Reference： [1] Chemistry Letters, 1984, p. 1117 - 1120

5
[ 72925-15-6 ]
[ 100-39-0 ]
[ 5747-92-2 ]

Reference： [1] Molecules, 2017, vol. 22, # 10,

6
[ 5733-87-9 ]
[ 5747-92-2 ]

Reference： [1] Journal of the American Chemical Society, 1982, vol. 104, # 3, p. 799 - 807

7
[ 5731-17-9 ]
[ 5747-92-2 ]

Reference： [1] Patent: US5405853, 1995, A,
[2] Patent: US5686463, 1997, A,

8
[ 50-00-0 ]
[ 17136-36-6 ]
[ 140-88-5 ]
[ 5747-92-2 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1988, # 3, p. 579 - 583
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 2, p. 233 - 241

9
[ 65950-40-5 ]
[ 140-88-5 ]
[ 5747-92-2 ]

Reference： [1] Synthetic Communications, 2002, vol. 32, # 6, p. 935 - 939

10
[ 53215-95-5 ]
[ 5747-92-2 ]

Reference： [1] Chemistry Letters, 1984, p. 1117 - 1120
[2] Chemistry Letters, 1984, p. 1117 - 1120

11
[ 144964-17-0 ]
[ 140-88-5 ]
[ 5747-92-2 ]

Reference： [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 2, p. 91 - 98
[2] Journal of the Chemical Society, Chemical Communications, 1992, # 18, p. 1313 - 1314
[3] Tetrahedron Letters, 1993, vol. 34, # 30, p. 4861 - 4864
[4] Tetrahedron Letters, 1993, vol. 34, # 30, p. 4861 - 4864

12
[ 59378-87-9 ]
[ 5747-92-2 ]

Reference： [1] Molecules, 2017, vol. 22, # 10,

13
[ 140-88-5 ]
[ 5747-92-2 ]

Reference： [1] Patent: WO2005/26165, 2005, A1, . Location in patent: Page/Page column 69

14
[ 5747-92-2 ]
[ 80028-44-0 ]

Reference： [1] Journal of the American Chemical Society, 1982, vol. 104, # 3, p. 799 - 807

15
[ 5747-92-2 ]
[ 276872-86-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 8, p. 2150 - 2155

[ 5747-92-2 ] Synthesis Path-Downstream 1~88

1
[ 5733-87-9 ]
[ 5747-92-2 ]

Reference： [1]Journal of the American Chemical Society,1982,vol. 104,p. 799 - 807

2
[ 5747-92-2 ]
[ 72925-15-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;palladium 10% on activated carbon; In ethanol; under 3102.97 Torr; for 6.0h;	A solution of1-benzyl-pyrrolidine-3-carboxylic acid ethyl ester (10.00 g, 42.9 mmol) in ethanol (200 mL) was hydrogenated in the presence of 10% Pd/C (2.0 g) at 60 psi for 6 hours. The resulting suspension was filtered through celite, washed withCH2C12, and concentrated under reduced pressure to leave the crude <Desc/Clms Page number 130>title compound(7. 12 g, 100%yield). 1H NMRa(CDC13) 4.16 (q, 2H),3. 02- 3.17 (m, 3H), 2.82-2. 94 (m, 2H), 1.91-2. 07 (m, 2H), 1.26 (t, 3H). LCMS(APCI+) 144 (100%, MH+).
100%	With hydrogen;palladium 10% on activated carbon; In ethanol; under 3102.97 Torr; for 6.0h;	A solution of1-benzyl-pyrrolidine-3-carboxylic acid ethyl ester (10.00g, 42.9 mmol) in ethanol (200 mL) was hydrogenated in the presence of 10%Pd/C (2.0 g) at 60 psi for 6 hours. The resulting suspension was filtered through celite, washed withCH2Cl2, and concentrated under reduced pressure to leave the crude <Desc/Clms Page number 158>title compound (7.12 g, 100%yield). 1H NMRO(CDCl3) 4.16 (q,2H), 3.02- 3.17(m, 3H), 2.82-2. 94 (m, 2H), 1.91-2. 07 (m, 2H), 1.26 (t, 3H). LCMS(APCI+) 144 (100%,Moi+).
99%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 60℃; under 2068.65 Torr; for 16.0h;	Palladium hydroxide on carbon (10% by weight, 32 g) was added to a solution of 1-benzyl-pyrrolidine-3-carboxylic acid ethyl ester (320 g, 1.37 mol) in ethanol (3000 mL) and hydrogenated (40 psi, 60 C.) for 16 hours. The reaction mixture was filtered through Arbocel then the filtrate was concentrated under reduced pressure to afford the title compound as a brown oil (195 g, 99%). 1H NMR (400 MHz, CDCl3) delta: 1.23 (t, 3H), 1.90-2.00 (m, 2H), 2.79-2.88 (m, 2H) 3.00-3.12 (m, 3H), 4.10 (q, 2H)

	In methanol; ethanol; dichloromethane;	(c) 3-Carboethoxypyrrolidine A solution of 1-benzyl-3-carboethoxypyrrolidine (2 g, 8.6 mmol) in ethanol (75 ml) was subjected to hydrogenolysis over Pd(OH)2 on a parr shaker for 48 hr. The catalyst was filtered off, the solvent removed under vacuum, and the residue chromatographed through alumina using dichloromethane/methanol (85:15) as eluant, to give the title product as a clear liquid (0.6 g); delta(60 MHz, CDCl3) 1.20 (3H, t, J=7 Hz, OCH2 CH3); 1.70-2.30 (2H, m, CH2); 2.50-3.20 (5H, m, 2*CH2 --N, and CH--CO2 Et); 4.10 (2H, q, J=7 Hz, OCH2 CH3).
	With hydrogen;palladium dihydroxide; In acetic acid;	A solution of 159C (210 mg, 0.85 [MMOL)] in [ACOH] (10 [ML)] was treated with Pd (OH) (100 mg) and stirred under H2 overnight. The reaction mixture was filtered through celite and concentrated to provide 159D.

Reference： [1]Patent: WO2005/49602,2005,A1 .Location in patent: Page/Page column 89; 90; 129; 130
[2]Patent: WO2005/49605,2005,A1 .Location in patent: Page/Page column 117; 118; 157; 158
[3]Patent: US2010/120793,2010,A1 .Location in patent: Page/Page column 36
[4]Journal of Medicinal Chemistry,1992,vol. 35,p. 233 - 241
[5]Patent: US5686463,1997,A
[6]Patent: WO2003/103669,2003,A1 .Location in patent: Page 71-72

3
[ 5747-92-2 ]
[ 128259-47-2 ]

Reference： [1]Synthesis,1994,vol. 1,p. 465 - 467

4
[ 5747-92-2 ]
[ 80028-44-0 ]

Reference： [1]Journal of the American Chemical Society,1982,vol. 104,p. 799 - 807

5
[ 50-00-0 ]
[ 17136-36-6 ]
[ 140-88-5 ]
[ 5747-92-2 ]

Reference： [1]Bulletin de la Societe Chimique de France,1988,p. 579 - 583
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 233 - 241

6
[ 93102-05-7 ]
[ 140-88-5 ]
[ 5747-92-2 ]

Reference： [1]Synthesis,2006,p. 2646 - 2648
[2]Tetrahedron Letters,2010,vol. 51,p. 1026 - 1029
[3]Chemistry Letters,1984,p. 1117 - 1120
[4]Journal of Organic Chemistry,2019,vol. 84,p. 5877 - 5885
[5]Journal of Organic Chemistry,2019

7
[ 93102-06-8 ]
[ 140-88-5 ]
[ 5747-92-2 ]

Reference： [1]Chemistry Letters,1984,p. 1117 - 1120

8
[ 144964-17-0 ]
[ 140-88-5 ]
[ 5747-92-2 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 91 - 98
[2]Journal of the Chemical Society. Chemical communications,1992,p. 1313 - 1314
[3]Tetrahedron Letters,1993,vol. 34,p. 4861 - 4864
[4]Tetrahedron Letters,1993,vol. 34,p. 4861 - 4864

9
[ 5747-92-2 ]
[ 501-53-1 ]
[ 848413-99-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	In chloroform; for 4h;Heating / reflux;	To a solution of N-Benzyl Pyrrolidine-3-carboxylic acid ethyl ester (4.0 g, 17.14 mmol) in chloroform (40 mL) was added benzyl CHLOROFORMATE (4.94 mL, 34.6 mmol). The mixture was heated at reflux for 4 hours. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (1: 2 ethyl acetate: hexanes to give the title compound (Yield: 4.0 g, 85%). LH NMR (200 MHz, CDC13) 8 7.43-7. 28 (M, 5H), 5.12 (s, 2H), 4.24-4. 08 (dd, 2H), 3.75- 3.35 (m, 4H), 3.15-2. 95 (m, 1H), 2.22-2. 06 (m, 2H), 1.32-1. 20 (t, 3H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2150 - 2155
[2]Patent: WO2005/26165,2005,A1 .Location in patent: Page/Page column 136

10
[ 5747-92-2 ]
C₂₂H₂₅FN₄O₄ [ No CAS ]