[ CAS No. 316141-37-4 ] {[proInfo.proName]}

Name: 316141-37-4|1-Boc-2-Ethynylpyrrolidine|95%
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Quality Control of [ 316141-37-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 316141-37-4 ]

Product Details of [ 316141-37-4 ]

CAS No. :	316141-37-4	MDL No. :	MFCD12032142
Formula :	C₁₁H₁₇NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MKFYNQAKTJFISL-UHFFFAOYSA-N
M.W :	195.26	Pubchem ID :	14730283
Synonyms :

Calculated chemistry of [ 316141-37-4 ]

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 :	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 :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.91
Log Po/w (XLOGP3) :	1.75
Log Po/w (WLOGP) :	1.72
Log Po/w (MLOGP) :	1.9
Log Po/w (SILICOS-IT) :	1.44
Consensus Log Po/w :	1.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.96
Solubility :	2.17 mg/ml ; 0.0111 mol/l
Class :	Very soluble
Log S (Ali) :	-1.99
Solubility :	2.01 mg/ml ; 0.0103 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.08
Solubility :	16.2 mg/ml ; 0.083 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.09

Safety of [ 316141-37-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

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.

Upstream synthesis route of [ 316141-37-4 ]
Downstream synthetic route of [ 316141-37-4 ]

[ 316141-37-4 ] Synthesis Path-Upstream 1~2

1
[ 90965-06-3 ]
[ 316141-37-4 ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: With diisobutylaluminium hydride In n-heptane; dichloromethane at -78℃; for 1.25 h; Stage #2: With methanol In n-heptane; dichloromethane	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 58percent yield. ¹H NMR (CDCl₃, 400 MHz): δ 1.48 (s, 9H), 1.90-2.22 (m, 4H), 3.31-3.49 (m, 2H), 4.42-4.52 (m, IH).

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

2
[ 59378-82-4 ]
[ 90965-06-3 ]
[ 316141-37-4 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 818 - 826

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

1
[ 316141-37-4 ]
C₇H₉NO₂ [ No CAS ]

Reference： [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 ]

Reference： [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).

Reference： [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).

Reference： [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).

Reference： [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.

Reference： [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).

Reference： [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).

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

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

Yield	Reaction Conditions	Operation in experiment
		Intermediate 41: tert-Butyl 2-tribut lstannanylethynyl-pyrrolidine-l-carboxylate[00292] n-Butyllithium (1.6M in hexanes, 12.3mL) was added over 2 minutes to a stirred solution of tert-butyl 2-ethynylpyrrolidine-l-carboxylate (3.65g) in anhydrous THF (80mL) at - 78C under nitrogen and then the mixture was allowed to warm to -30C over one hour.Tributyltin chloride (6.41g) was then added dropwise at -30C and the mixture was allowed to warm to -10C and quenched by addition of saturated sodium bicarbonate solution. The layers were separated and the organic layer was dried (Na2S04) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-5% to give tert-butyl 2- tributylstannanylethynylpyrrolidine-l-carboxylate (5.54g) as a colourless oil.1H NMR (CDCI3) delta: 4.35-4.6 (1H, br, s), 3.45 (1H, br, s), 3.29 (1H, br, s), 1.93-2.12 (3H, br, m), 1.86 (1H, br, s), 1.49-1.59 (6H, m), 1.48 (9H, s) 1.25-1.40 (6H, m), 0.95 (6H, m), 0.89 (9H, t).

Reference： [1]Patent: WO2012/154678,2012,A1 .Location in patent: Page/Page column 83

11
[ 316141-37-4 ]
[ 1411982-78-9 ]