[ CAS No. 119020-03-0 ] {[proInfo.proName]}

Name: 119020-03-0|Benzyl 2-(aminomethyl)pyrrolidine-1-carboxylate|95%
Brand: Ambeed
SKU: A117543
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Quality Control of [ 119020-03-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 119020-03-0 ]

Product Details of [ 119020-03-0 ]

CAS No. :	119020-03-0	MDL No. :	MFCD06658394
Formula :	C₁₃H₁₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NQGRCKNDDGCZPV-UHFFFAOYSA-N
M.W :	234.29	Pubchem ID :	4712622
Synonyms :

Calculated chemistry of [ 119020-03-0 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.46
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	69.33
TPSA :	55.56 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) :	-6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.68
Log Po/w (XLOGP3) :	1.24
Log Po/w (WLOGP) :	1.21
Log Po/w (MLOGP) :	1.41
Log Po/w (SILICOS-IT) :	1.25
Consensus Log Po/w :	1.56

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.01
Solubility :	2.32 mg/ml ; 0.00989 mol/l
Class :	Soluble
Log S (Ali) :	-2.0
Solubility :	2.32 mg/ml ; 0.00989 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.76
Solubility :	0.408 mg/ml ; 0.00174 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.61

Safety of [ 119020-03-0 ]

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 [ 119020-03-0 ]

* 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.

Upstream synthesis route of [ 119020-03-0 ]
Downstream synthetic route of [ 119020-03-0 ]

[ 119020-03-0 ] Synthesis Path-Upstream 1~8

1
[ 141774-67-6 ]
[ 119020-03-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With water; triphenylphosphine In tetrahydrofuran at 20℃; for 12 h;	General procedure: To a stirred soln of azide derivative 9a or 9b (4.03 mmol) in THF (1 mL) was added solid Ph3P (4.03 mmol) and H2O (6.04 mmol). The resulting solution was stirred for 12 h at r.t., then concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (MeOH–CH2Cl2, 9:1).

Reference： [1] Synthetic Communications, 2011, vol. 41, # 17, p. 2517 - 2523
[2] Synthesis (Germany), 2013, vol. 45, # 17, p. 2458 - 2468
[3] Tetrahedron Letters, 2010, vol. 51, # 1, p. 209 - 212
[4] Tetrahedron Letters, 1991, vol. 32, # 49, p. 7183 - 7186

2
[ 34079-31-7 ]
[ 119020-03-0 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: With borane In tetrahydrofuran at 0℃; for 7 h; Heating / reflux Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0℃; for 6 h; Heating / reflux Stage #3: With sodium hydroxide In tetrahydrofuran; water	A typical procedure for the reduction is as follows: starting with a solution of (S)-2-carbamoyl-l-7V-CBz-pyrrolidine (0.5g, 2mmol) in THF (10ml), borane BH₃ (12ml, 12mmol, 1 .OM THF solution) was added slowly at 0°C under N2. The resulting solution was heated to reflux for 7 hours, then cooled to 0°C, followed by slow addition of 4.5mL of 12N HC1 to destroy the B-N complex. The mixture was heated to reflux for 6 hours, cooled to roomed temperature (RT), then was neutralized to ph8 by a WNaOH aqueous solution. After THF and water were removed under reduced pressure, the crude product was purified by use offlash silica gel column chromatography (1/10 = MeOH/CHzC^) to afford a clear, slightlyyellow oil in 74percent yield (348mg).

Reference： [1] Chemistry - A European Journal, 2006, vol. 12, # 16, p. 4321 - 4332
[2] Patent: WO2006/7586, 2006, A1, . Location in patent: Page/Page column 31-32

3
[ 63808-36-6 ]
[ 119020-03-0 ]

Reference： [1] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5260 - 5266

4
[ 6216-63-3 ]
[ 119020-03-0 ]

Reference： [1] Tetrahedron Letters, 1991, vol. 32, # 49, p. 7183 - 7186
[2] Synthetic Communications, 2011, vol. 41, # 17, p. 2517 - 2523
[3] Synthesis (Germany), 2013, vol. 45, # 17, p. 2458 - 2468

5
[ 1148-11-4 ]
[ 119020-03-0 ]

6
[ 72500-24-4 ]
[ 119020-03-0 ]

Reference： [1] Tetrahedron Letters, 1991, vol. 32, # 49, p. 7183 - 7186
[2] Synthetic Communications, 2011, vol. 41, # 17, p. 2517 - 2523

7
[ 501-53-1 ]
[ 119020-03-0 ]

Reference： [1] Tetrahedron Letters, 1991, vol. 32, # 49, p. 7183 - 7186

8
[ 147-85-3 ]
[ 119020-03-0 ]

Reference： [1] Tetrahedron Letters, 1991, vol. 32, # 49, p. 7183 - 7186

[ 119020-03-0 ] Synthesis Path-Downstream 1~55

1
[ 141774-67-6 ]
[ 119020-03-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With water; triphenylphosphine; In tetrahydrofuran; at 20℃; for 12h;	General procedure: To a stirred soln of azide derivative 9a or 9b (4.03 mmol) in THF (1 mL) was added solid Ph3P (4.03 mmol) and H2O (6.04 mmol). The resulting solution was stirred for 12 h at r.t., then concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (MeOH-CH2Cl2, 9:1).

Reference： [1]Synthetic Communications,2011,vol. 41,p. 2517 - 2523
[2]Synthesis,2013,vol. 45,p. 2458 - 2468
[3]Tetrahedron Letters,2010,vol. 51,p. 209 - 212
[4]Tetrahedron Letters,1991,vol. 32,p. 7183 - 7186

2
[ 358-23-6 ]
[ 119020-03-0 ]
[ 782495-19-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine; In dichloromethane; at 0 - 20℃; for 5.5h;	(iUSD)-2-(trifluoro methane sulfonylamino methyl)-l-./V-Cbz-pyrroIidme. To a solutionof (^-2-Ammomethyl-l-A/-Cbz-pyn:olidine (2.0 g, 8.55 mmol) and TEA (1.43 mL, 10.3mmol) in 40 mL of CaHz dried CHzCk was added trifluoromethanesulfonic anhydride (1.6mL, 9.4 mmol) dropwisely by a syringe pump over 1 h at 0 C under Na. The resultingsolution was stirred for 4.5 h at rt, then diluted with 80 mL of CHiCk and washed with 50mL of 1JVHC1 aqueous solution. The organic layer was dried over MgSO4, and concentratedin vacua. Flash chromatography (Ethyl Acetate/Hexane = 1/7) afforded a colorless oil in76% yield (2.38g, 6.50mmol). [a]D -27.7 (c 1.0, CHC13); .H NMR (500 MHz, CDC13): 5 7.68(s, 1H), 7.10-7.39 (m, 5H), 5.15 (q, 2H), 3.98-4.09 (m, 1H), 3.24-3.57 (m, 4H), 2.12 (m, 1H),1.88 (m, 2H), 1.67 (m, 1H); 13C NMR (125 MHz, CDC13): 8 157.7,136.2, 128.8,128.6,128.5, 128.3, 68.0, 58.1, 49.9, 47.5, 30.0, 24.1. HRMS (FAB) calcd for C^HigFsNzCUS (M +1) m/z 367.0939, found 367.0928.

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 7235 - 7238
[2]Angewandte Chemie - International Edition,2005,vol. 44,p. 1369 - 1371
[3]Patent: WO2006/7586,2006,A1 .Location in patent: Page/Page column 80; 92

3
[ 307-35-7 ]
[ 119020-03-0 ]
(S)-2-(perfluorooctane-sulfonylamino methyl)-1-N-Cbz-pyrrolidine [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 3077 - 3079

4
[ 375-72-4 ]
[ 119020-03-0 ]
(S)-2-(perfluorobutane-sulfonylamino methyl)-1-N-Cbz-pyrrolidine [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 3077 - 3079

5
[ 34079-31-7 ]
[ 119020-03-0 ]

Yield	Reaction Conditions	Operation in experiment
74%		A typical procedure for the reduction is as follows: starting with a solution of (S)-2-carbamoyl-l-7V-CBz-pyrrolidine (0.5g, 2mmol) in THF (10ml), borane BH3 (12ml, 12mmol, 1 .OM THF solution) was added slowly at 0C under N2. The resulting solution was heated to reflux for 7 hours, then cooled to 0C, followed by slow addition of 4.5mL of 12N HC1 to destroy the B-N complex. The mixture was heated to reflux for 6 hours, cooled to roomed temperature (RT), then was neutralized to ph8 by a WNaOH aqueous solution. After THF and water were removed under reduced pressure, the crude product was purified by use offlash silica gel column chromatography (1/10 = MeOH/CHzC^) to afford a clear, slightlyyellow oil in 74% yield (348mg).

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 4321 - 4332
[2]Patent: WO2006/7586,2006,A1 .Location in patent: Page/Page column 31-32

6
[ 119020-03-0 ]
N-(((2S,4R)-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-yl)methyl)-1,1,1-trifluoromethanesulfonamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 4321 - 4332
[2]Angewandte Chemie - International Edition,2005,vol. 44,p. 1369 - 1371
[3]Tetrahedron Letters,2004,vol. 45,p. 7235 - 7238

7
[ 119020-03-0 ]
(S)-2-(perfluorobutane-sulfonylamino methyl)-pyrrolidine [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 3077 - 3079

8
[ 119020-03-0 ]
(S)-2-(perfluorooctane-sulfonylamino methyl)-pyrrolidine [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 3077 - 3079

9
[ 6216-63-3 ]
[ 119020-03-0 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 7183 - 7186
[2]Synthetic Communications,2011,vol. 41,p. 2517 - 2523
[3]Synthesis,2013,vol. 45,p. 2458 - 2468

10
[ 72500-24-4 ]
[ 119020-03-0 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 7183 - 7186
[2]Synthetic Communications,2011,vol. 41,p. 2517 - 2523

11
[ 501-53-1 ]
[ 119020-03-0 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 7183 - 7186

12
[ 147-85-3 ]
[ 119020-03-0 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 7183 - 7186

13
[ 1148-11-4 ]
[ 119020-03-0 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 7183 - 7186
[2]Synthetic Communications,2011,vol. 41,p. 2517 - 2523
[3]Synthesis,2013,vol. 45,p. 2458 - 2468

14
[ 135422-90-1 ]
[ 119020-03-0 ]
(S)-1-Benzyloxycarbonyl-2-(1-oxo-3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propyl]-aminomethylpyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%		(A) Preparation of (S)-1-Benzyloxycarbonyl-2-(1-oxo-3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propyl]-aminomethylpyrrolidine (S)-2-Aminomethyl-1-benzyloxycarbonylpyrrolidine (234 mg) and 3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]-propionic acid (259 mg) were reacted in the same manner as in Reference Example 25 to obtain 424 mg of the ojective compound (yield: 89%). Property: Oily Mass Spectrometric Analysis: Molecular formula: C25H37N3O6 Calculated: 475.2682 Found: 475.2701 NMR(delta, CDCl3): 0.98 (3H,s), 1.04 (3H,s), 1.42 (3H,s), 1.46 (3H,s), 1.62-2.13 (4H,m),2.30-2.44 (2H,m), 3.16-3.62 (4H,m), 3.27 (1H,d,J=12Hz), 3.68 (1H,d,J=12Hz), 3.92-4.09 (1H,m), 4.07 (1H,s), 5.07-5.24 (2H,m), 7.05-7.16 (1H,m), 7.17-7.25 (1H,m), 7.28-7.48 (5H,m)

Reference： [1]Patent: EP421441,1991,A2

15
[ 75-15-0 ]
[ 119020-03-0 ]
[ 1172596-79-0 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5260 - 5266

16
[ 63808-36-6 ]
[ 119020-03-0 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5260 - 5266

17
[ 119020-03-0 ]
[ 1499-21-4 ]
[ 1206881-76-6 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 209 - 212

18
[ 119020-03-0 ]
[ 74157-87-2 ]
C₂₇H₂₉N₃O₂ [ No CAS ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4156 - 4159

19
[ 119020-03-0 ]
[ 98-59-9 ]
C₂₀H₂₄N₂O₄S [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 396 - 402

20
[ 119020-03-0 ]
[ 98-59-9 ]
(S)-4-methyl-N-(pyrrolidinyl-2-methyl)benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 396 - 402

21
[ 1120-71-4 ]
[ 119020-03-0 ]
C₁₆H₂₄N₂O₅S [ No CAS ]

Reference： [1]Synlett,2011,p. 495 - 498

22
[ 81-08-3 ]
[ 119020-03-0 ]
C₂₀H₂₂N₂O₆S [ No CAS ]

Reference： [1]Synlett,2011,p. 495 - 498

23
[ 119020-03-0 ]
[ 1304774-61-5 ]

Reference： [1]Synlett,2011,p. 495 - 498

24
[ 23165-29-9 ]
[ 119020-03-0 ]
[ 1321848-92-3 ]

Reference： [1]Synthetic Communications,2011,vol. 41,p. 2517 - 2523

25
[ 1121-60-4 ]
[ 119020-03-0 ]
C₁₉H₂₁N₃O₂ [ No CAS ]