316141-37-4|1-Boc-2-Ethynylpyrrolidine| Ambeed

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Quality Control of [ 316141-37-4 ] Purity: 95% SDS Specification

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Product Details of [ 316141-37-4 ]

CAS No. :	316141-37-4
Formula :	C₁₁H₁₇NO₂
M.W :	195.26
SMILES Code :	CC(C)(C)OC(=O)N1CCCC1C#C
MDL No. :	MFCD12032142
InChI Key :	MKFYNQAKTJFISL-UHFFFAOYSA-N
Pubchem ID :	14730283

Safety of [ 316141-37-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 316141-37-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	0
Fraction Csp3	0.73
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	59.56
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.54 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.91
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.75
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.72
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.9
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.44
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.94

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.96
Solubility	2.17 mg/ml ; 0.0111 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.99
Solubility	2.01 mg/ml ; 0.0103 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.08
Solubility	16.2 mg/ml ; 0.083 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.25 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.09

Application In Synthesis of [ 316141-37-4 ]

* 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 [ 316141-37-4 ]

[ 316141-37-4 ] Synthesis Path-Downstream 1~26

1
[ 316141-37-4 ]
C₇H₉NO₂ [ No CAS ]

References: [1]Synlett,2006,p. 2727 - 2730.

2
[ 316141-37-4 ]
[ 2461-42-9 ]
(2-{1-[2-hydroxy-3-(naphthalen-1-yloxy)-propyl]-1H-[1,2,3]triazol-4-yl}pyrrolidin-1-yl)carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 9822 - 9825.

3
[ 316141-37-4 ]
[ 627-05-4 ]
[ 103-71-9 ]
3-n-propyl-5-(N-(tert-butyloxycarbonyl)-2(S)-pyrrolidinyl)isoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine; In benzene;	9 a. 5-(N-t-butyloxycarbonyl-2(S)-pyrrolidinyl)-3-propyl-isoxazole Under a nitrogen atmosphere with stirring, (2S)-Ethynyl-N-t-butyloxycarbonylpyrrolidine (1.23 g, 6.30 mmol) and phenyl isocyanate (1.55 mL, 14.2 mmol) were combined in 2.6 mL of benzene. A solution of nitrobutane (1.0 mL, 9.45 mmol) in 3.0 mL of benzene and 7 drops of triethylamine was then added to the solution. A precipitate began to form about 2 to 3 minutes after addition was complete. The reaction mixture was stirred at ambient temperature for 2 hours, heated at reflux for 1.5 hours, allowed to cool to ambient temperature and stirred overnight. The reaction mixture was then filtered and the filter cake washed with benzene. The filtrate was concentrated in vacuo and the residue was purified using flash chromatography on silica gel eluted with ethyl acetate/hexane (1:12?1:10?1:8) to give 1.07 g (61% yield) of the title compound (9a) as a clear yellow oil. [alpha]23D =-51.4 (c 0.80, MeOH). MS (DCl/NH3) m/e 281 (M+H)+, 298 (M+NH4)+. 1 H NMR (DMSO-d6, 500 MHz, 100 C.) delta0.93 (t, J=7.5 Hz, 3H), 1.34 (s, 9H), 1.64 (qt, J=7.5 Hz, 7.3 Hz, 2H), 1.88-1.95 (m, 3H), 2.22-2.27 (m, 1H), 2.56 (t, J=7.3 Hz, 2H), 3.37-3.46 (m, 2H), 4.92 (dd, J=8.3 Hz, 2.6 Hz, 1H), 6.08 (s, 1H).

References: [1]Patent: US5409946,1995,A .

4
[ 316141-37-4 ]
Dibromoformaldoxime [ No CAS ]
3-Bromo-5-(1-methyl-2(S)-pyrrolidinyl)-isoxazole hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.5%	With sodium hydrogencarbonate; In water; ethyl acetate;	EXAMPLE 27 3-Bromo-5-(1-methyl-2(S)-pyrrolidinyl)-isoxazole hydrochloride 27 a. -3-Bromo-5-(1-BOC-2(S)-pyrrolidinyl)-isoxazole A 7.151 g (36.62 mmol) sample of (2S)-ethynyl-N-t-butyloxycarbonyl-pyrrolidine (from Example 1 c above) was dissolved in 200 mL of ethyl acetate, and 22 mL of water, 18.46 g (219.7 mmol) of NaHCO3, and 14.80 g (72.9 mmol) of dibromoformaldoxime (prepared according to Vyas et al., Tett. Lett., 25:487-490 (1984)), and the mixture was stirred at room temperature for 90 hr. The mixture was diluted with 100 mL of ethyl acetate, and washed with water and brine, then the solvent was dried over MgSO4 and evaporated to leave the crude product as a brown oil. The residue was purified by flash chromatography over silica gel, eluding with 1:6 ethyl acetate:hexane. Removal of the solvent gave 8.998 g of the title product as a yellow oil (77.5% yield). MS m/e: 278, 280 (M-C4 H9 +NH4)+, 317, 319 (M+H)+, 334, 336 (M+NH4)+. NMR (CDCl3) delta: 1.36, 1.46 (two singlets, 9H), 1.94-2.35 (m, 4H), 3.4-3.6 (m, 2H), 4.92-5.06 (two broad doublets, 1H), 6.13, 6.19 (two singlets, 1H).

References: [1]Patent: US5409946,1995,A .

5
[ 123-75-1 ]
[ 316141-37-4 ]
(R)-2-[3-(1-Pyrrolidinyl)-1-propynyl]-1-pyrrolidine-carboxylic acid,1,1-dimethylethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With paraformaldehyde;copper(I) chloride; In 1,4-dioxane; acetic acid;	EXAMPLE 5 (R)-2-[3-(1-Pyrrolidinyl)-1-propynyl]-1-pyrrolidine-carboxylic acid, 1,1-dimethylethyl ester A mixture of 3.5 g of <strong>[316141-37-4](R)-2-ethynyl-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester</strong>, 75 ml dry dioxane, 3.0 ml pyrrolidine, 1.43 g of paraformaldehyde, 7.0 ml of glacial acetic acid and 50 mg of cuprous chloride is stirred at room temperature for 15 minutes then refluxed for 2 hours. The reaction is cooled and concentrated in vacuo. The residue is partitioned between water and methylene chloride and the pH of the mixture is adjusted to pH 11 with ammonium hydroxide. The basified reaction is extracted with methylene chloride and dried over sodium sulfate. The methylene chloride solution is passed over hydrous magnesium silicate and concentrated in vacuo to give 5.65 g of a dark yellow oil. The product is purified by chromatography using deactivated alumina as the absorbant, to give 0.55 g of the product as a pale yellow oil, [alpha]D26 =+100.6+-0.8 (C=1.22%, methylene chloride).
3.8 g (88%)	With paraformaldehyde;copper(I) chloride; In 1,4-dioxane; methanol; chloroform;	Part A. (R)-t-Butyl 2-[3-(1-pyrrolidinyl)-1-propynyl]-1-pyrrolidine-carboxylate A mixture of <strong>[316141-37-4](R)-t-butyl 2-ethynyl-1-pyrrolidinecarboxylate</strong> (4.2 g, 0.02 mol), pyrrolidine (2.1 g, 0.03 mol), paraformaldehyde (0.9 g, 0.03 mol), and cuprous chloride (30 mg), in dioxane (30 mL) was stirred at 70 C. for 40 min. The dioxane was removed and the residual oil was dissolved in chloroform and chromatographed on silica gel using 2 to 5% methanol:chloroform as eluant to give 3.8 g (88%) of pure product as an oil. [a]D +129 (c 0.51, MeOH). An aliquot of the product was converted to the oxalate salt, m.p. 78 C. (dec) from methanol:ether. [alpha]D +95 (c 0.91, MeOH).

References: [1]Patent: US5001142,1991,A .
[2]Patent: US5137905,1992,A .

Yield	Reaction Conditions	Operation in experiment
84%		Part B. (S)-t-Butyl 2-ethynyl-1-pyrrolidinecarboxylate This product was prepared in 84% yield using the above procedure by substituting (S)-t-butyl 2-(2,2-dibromoethenyl)-1-pyrrolidinecarboxylate for (R)-t-butyl 2-(2,2-dibromoethenyl)-1-pyrrolidinecarboxylate.

7
(R)-2-(2,2-dibromoethenyl)-1pyrrolidinecarboxylic acid,1,1-dimethylethyl ester [ No CAS ]
[ 316141-37-4 ]

Yield	Reaction Conditions	Operation in experiment
6.9 g (88%)	With n-butyllithium; In tetrahydrofuran; methanol; ethyl acetate;	Part A. (R)-t-Butyl 2-ethynyl-1-pyrrolidinecarboxylate Butyl lithium (48 mL, 0.08 mol) was added at -78 C. to a stirred solution of (R)-t-butyl 2-(2,2-dibromoethenyl)-1-pyrrolidinecarboxylate (14.2 g, 0.04 mol) in dry THF (300 mL). The color turned to dark yellow. After 15 min. methanol (10 mL) and ethyl acetate (10 mL) were added and the solution was allowed to warm to room temperature. The solvent was removed and the residue was partitioned between ethyl acetate and water. The ethyl acetate phase was concentrated and applied to a silica gel column. Elution with ethyl acetate:Skellysolve B (1:10) gave 6.9 g (88%) of product as a yellow oil.

References: [1]Patent: US5137905,1992,A .

8
[ 316141-37-4 ]
2-ethynyl-pyrrolidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; water; In diethyl ether; at 20℃; for 36.0h;	Step 2: Preparation of 2-ethynyl-pyrrolidine hydrochloride 63. To a solution of compound 62 (870 mg, 1 eq.) in diethyl ether was added 37% aqueous HCl (1.15 mL). The mixture was stirred at room temperature for 1.5 day, and then evaporated and sonicated in diethyl ether to yield compound 63 as a beige solid in quantitative yield. 1H NMR (DMSO-J6, 400 MHz) delta 2.02-2.22 (m, 4H), 3.40-3.49 (m, 2H), 4.32-4.42 (m, IH).

References: [1]Patent: WO2009/14730,2009,A1 .Location in patent: Page/Page column 115.

9
2-[(methoxymethylamino) carbonyl]-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester [ No CAS ]
[ 90965-06-3 ]
[ 316141-37-4 ]

Yield	Reaction Conditions	Operation in experiment
58%		Step 1: Preparation of Boc-2-ethynyl -pyrrolidine 62. To a solution of 2-(methoxy-methyl-carbamoyl)-pyrrolidine-l-carboxylic acid-tert-butyl ester 61 (2 g, 1 eq.) in dry DCM (15 mL) was added 1 M DIBAL solution in heptane (9.3 mL, 1.2 eq.) at -78 0C under nitrogen over 15 min. After 1 hr, the mixture was quenched with MeOH (7 mL) and then allowed to warm up to 0 0C. Bestmann-Ohira reagent (1.8 g, 1.2 eq.), K2CO3 (2.14 g, 2 eq.), and MeOH (7 mL) were added and the mixture was stirred at room temperature for 2 days. Rochelle's salt (1.2 eq.) in water was added and the mixture was vigorously stirred for <n="116"/>2 hrs. The mixture was then extracted with EtOAc. Organics were dried over Na2SO4 and concentrated under reduced pressure to yield compound 62 as colorless oil in 58% yield. 1H NMR (CDCl3, 400 MHz): delta 1.48 (s, 9H), 1.90-2.22 (m, 4H), 3.31-3.49 (m, 2H), 4.42-4.52 (m, IH).

References: [1]Patent: WO2009/14730,2009,A1 .Location in patent: Page/Page column 114-115.

10
[ 316141-37-4 ]
[ 1461-22-9 ]
[ 1411983-09-9 ]