180307-56-6|tert-Butyl 4-vinylpiperidine-1-carboxylate| Ambeed

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Quality Control of [ 180307-56-6 ] Purity: 98% SDS Specification

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Product Details of [ 180307-56-6 ]

CAS No. :	180307-56-6
Formula :	C₁₂H₂₁NO₂
M.W :	211.30
SMILES Code :	C(=O)(OC(C)(C)C)N1CCC(CC1)C=C
MDL No. :	MFCD11036128
InChI Key :	LKUCYFONIRHGSQ-UHFFFAOYSA-N
Pubchem ID :	10910832

Safety of [ 180307-56-6 ]

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

Computational Chemistry of [ 180307-56-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	0
Fraction Csp3	0.75
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	65.73
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.	3.09
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	2.5
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.44
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.	2.18
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	1.9
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.42

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.46
Solubility	0.731 mg/ml ; 0.00346 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.77
Solubility	0.362 mg/ml ; 0.00171 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-1.73
Solubility	3.97 mg/ml ; 0.0188 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.	-5.81 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	0.0
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)	2.18

Application In Synthesis of [ 180307-56-6 ]

* 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 [ 180307-56-6 ]

[ 180307-56-6 ] Synthesis Path-Downstream 1~35

1
[ 180307-56-6 ]
{4-[6-bromo-1-(4-fluoro-benzyl)-1H-indazol-3-yl]-piperidin-1-yl}-acetic acid tert-butyl ester [ No CAS ]
[ 3375-31-3 ]
[ 6163-58-2 ]
[ 180307-57-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; triethylamine; lithium chloride; In N,N-dimethyl-formamide;	(x) 4-{2-[3-(1-tert-Butoxycarbonylmethyl-piperidin-4-yl)-1-(4-fluoro-benzyl)-1H-indazol-6-yl]-(E)-vinyl}-piperidine-1-carboxylic acid tert-butyl ester A stirred mixture of {4-[6-bromo-1-(4-fluoro-benzyl)-1H-indazol-3-yl]-piperidin-1-yl}-acetic acid tert-butyl ester (286 mg, 0.57 mmol), <strong>[180307-56-6]4-vinyl-piperidine-1-carboxylic acid tert-butyl ester</strong> (120 mg, 0.57 mmol), lithium chloride (24 mg, 0.57 mmol), triethylamine (0.24 ml, 1.71 mmol), palladium (II) acetate (8 mg 0.03 mmol), tri-o-tolylphosphine (35 mg, 0.11 mmol), and DMF (5 ml) was heated at 105 (oil-bath temperature) under nitrogen for 18 h. When cool, the mixture was evaporated in vacuo, treated with aqueous saturated sodium bicarbonate (20 ml), and extracted with ethyl acetate (2*20 ml). The combined, dried (Na2 SO4) organic extracts were evaporated, and the residue purified by flash chromatography over silica gel (Merck 9385). Elution with ethyl acetate --cyclohexane (1:2) afforded impure fractions and pure fractions (I). The impure fractions were purified by flash chromatography over silica gel (Merck-9385) eluding with ethyl acetate--cyclohexane (gradient 1:4 to 1:2) to give pure fractions (II). The pure fractions (I) and (II) were combined to give the title compound as a pale yellow oil (195 mg).

References: [1]Patent: US5861414,1999,A .

2
[ 169457-73-2 ]
[ 180307-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran; diethyl ether;	(ix) 4-Vinyl-piperidine-1-carboxylic acid tert-butyl ester A solution of 4(2-bromo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (81.5 g 0.279 mol) in dry tetrahydrofuran (1000 ml) under nitrogen at 20 was treated portionwise, over 30 min, with potassium tert-butoxide (63.2 g 0.563 mol). The mixture was stirred at 25 for 3 h and partitioned between saturated aqueous ammonium chloride (1000 ml) and diethyl ether (500 ml). The aqueous phase was extracted with diethyl ether (4*500 ml) and the combined, dried (MgSO4) extracts were evaporated in vacuo. The residue was purified by flash column chromatography on silica gel (Merck 9385) eluant cyclohexane: diethyl ether (19:1) to give the title compound as an orange oil (37.1 g, 0.176 mol, 63%). Mass spectrum m/z=212 ?MH+!

References: [1]Patent: US5861414,1999,A .

4
[ 186581-53-3 ]
[ 180307-56-6 ]
[ 208245-60-7 ]

Yield	Reaction Conditions	Operation in experiment
	palladium diacetate; In diethyl ether; at 0 - 20℃; for 5.0h;	1-M ethyl-3-nitro-1-nitrosoguanidine (3.00 g, 20.4 mmol) was added in small portions with agitation to a mixture of 5M aqueous NaOH solution (14 ml) and ether (70 ml), cooled to 0 C. The yellow ether layer was decanted into a flask precooled in an ice bath and containing a few KOH pellets for drying. To a solution of olefin 20 (0.20 g, 0.95 mmol) in ether (5 ml) cooled to 0 C. was added Pd(OAc)2 (0.006 g, 0.03 mmol), followed by the ethereal CH2N2 solution in portions (prepared as described above), and the reaction mixture was stirred at rt for 5 hr. It was quenched with AcOH and diluted with saturated aqueous NaHCO3 solution. The product was extracted with CH2Cl2 and the organic layer was dried over Na2SO4. Purification by flash chromatography (CH2Cl2) provided 0.16 g of 21 as a clear liquid.

References: [1]Patent: US2007/10513,2007,A1 .Location in patent: Page/Page column 14.

5
[ 19493-09-5 ]
[ 137076-22-3 ]
[ 180307-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; hexanes; at -78 - 20℃; for 0.5h;	To a suspension of methyltriphenylphosphonium bromide (1.76 g, 4.93 mmol) in THF (30 ml), cooled to -78 C., was added n-BuLi (1.88 ml of 2.5M soln. in hexanes; 4.68 mmol), and the mixture was stirred at -78 C. for 30 min and then at 0 C. for 45 min. It was cooled back to -78 C., and a solution of aldehyde 6 (0.50 g, 2.34 mmol) in THF (5 ml) was added. The reaction mixture was stirred at -78 C. for 30 min and warmed up to rt. It was quenched with water, and the product was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and purified by flash chromatography (0.5% MeOH/CH2Cl2) to provide 0.24 g of 20 as a clear oil. Step 2: BOC-deprotection and amide coupling steps as described in Example 2 were used to obtain the title compound MS (M+H): 347.

References: [1]Patent: US2007/10513,2007,A1 .Location in patent: Page/Page column 20.

6
[ 180307-56-6 ]
[ 1255208-31-1 ]
[ 1428478-86-7 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 130℃; for 2.0h;	Step B: tert-Butyl 4-[(E)-2-(4-Fluoro-l-oxo-13-dihydro-2-benzofuran-5-yl)ethenyllpiperidine- 1-carboxylate To a flask added 5-bromo-4-fluoro-2-benzofuran-l (3H)-one (0.10 g, 0.43 mmol) palladium(II)acetate (0.097 g, 0.043 mmol), triethylamine (0.12 mL, 0.88 mmol) and tert-butyl 4-ethyenylpiperidine-l-carboxylate (0.27 g, 1.2 mmol); the resulting mixture was then dissolved in DMF (15 mL) and heated in an oil bath at 130 C for 2 h. The flask was cooled to room temperature, diluted with EtOAc and washed with saturated sodium bicarbonate and water, then dried (Na2SC>4), filtered and adsorbed into silica gel. MPLC (hexanes/EtOAc = 1/1) purification provided tert-butyl 4-[(E)-2-(4-fluoro- 1 -oxo- 1 ,3-dihydro-2-benzofuran-5-yl)ethenyl]piperidine- 1-carboxylate. LC/MS: [(M+2)]+ =233.
	With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 130℃; for 2.0h;	[0171] To a flask added 5-bromo-4-fluoro-2-benzofuran-1(3H)-one (0.10 g, 0.43 mmol) palladium(II)acetate (0.097 g,0.043 mmol), triethylamine (0.12 mL, 0.88 mmol) and tent-butyl 4-ethyenylpiperidine-1-carboxylate (0.27 g, 1.2 mmol);the resulting mixture was then dissolved in DMF (15 mL) and heated in an oil bath at 130 C for 2 h. The flask was cooledto room temperature, diluted with EtOAc and washed with saturated sodium bicarbonate and water, then dried (Na2SO4),filtered and adsorbed into silica gel. MPLC (hexanes/EtOAc = 1/1) purification provided tert-butyl 4-[(E)-2-(4-fluoro-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethenyl]piperidine-1-carboxylate. LC/MS: [(M+2)]+ =233.

References: [1]Patent: WO2013/39802,2013,A1 .Location in patent: Page/Page column 49.
[2]Patent: EP2755656,2016,B1 .Location in patent: Paragraph 0171.

7
[ 51376-06-8 ]
[ 180307-56-6 ]
[ 1428478-48-1 ]
tert-butyl 4-[(Z)-2-(2,1,3-benzoxadiazol-5-yl)ethenyl]piperidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2013/39802,2013,A1 .Location in patent: Page/Page column 28.

8
[ 180307-56-6 ]
[ 1428478-45-8 ]

References: [1]Patent: EP2755656,2016,B1 .
[2]Patent: WO2013/39802,2013,A1 .

9
[ 180307-56-6 ]
[ 1428478-46-9 ]

References: [1]Patent: EP2755656,2016,B1 .
[2]Patent: WO2013/39802,2013,A1 .

10
[ 180307-56-6 ]
[ 586-78-7 ]
tert-butyl 4-[(E)-2-(4-nitrophenyl)ethenyl]piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichlorobis(tri-O-tolylphosphine)palladium; triethylamine; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Inert atmosphere; Microwave irradiation;	4- r(E)-2-(4-nitrophenyl)ethenyl1piperidinium Chloride Step A: fert-Butyl 4-r(E)-2-(4-nitrophenyl)ethenyl1piperidine-l-carboxylate tert-Butyl 4-ethenylpiperidine- 1 -carboxylate (0.50 g, 2.4 mmol), tra/?s-dichlorobis(tri-o- tolylphosphine) palladium (II) (0.050 g, 0.064 mmol), l-bromo-4-nitrobenzene (0.57 g, 2.8 mmol), and triethylamine (1.6 mL, 12 mmol) were added to a microwave tube, diluted with DMF (2 mL) and degassed under a stream of nitrogen. The tube was sealed and heated in the microwave to 130 C for 30 min. The resulting mixture was diluted with diethyl ether and washed successively with saturated sodium bicarbonate, water (2x), 1 N hydrochloric acid, and brine, then dried (MgS04), filtered and concentrated. The resulting tert-butyl 4-[(E)-2-(4- nitrophenyl)ethenyl]piperidine-l -carboxylate was used directly in the next step. LC/MS: [(M+l)]+ = 333.
	With dichlorobis(tri-O-tolylphosphine)palladium; triethylamine; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation; Inert atmosphere; Sealed tube;	[0070] tert-Butyl4-ethenylpiperidine-1-carboxylate (0.50 g, 2.4 mmol), trans-dichlorobis(tri-o-tolylphosphine) palladium(II) (0.050 g, 0.064 mmol), 1-bromo-4-nitrobenzene (0.57 g, 2.8 mmol), and triethylamine (1.6 mL, 12 mmol) were addedto a microwave tube, diluted with DMF (2 mL) and degassed under a stream of nitrogen. The tube was sealed andheated in the microwave to 130C for 30 min. The resulting mixture was diluted with diethyl ether and washed successivelywith saturated sodium bicarbonate, water (2x), 1 N hydrochloric acid, and brine, then dried (MgSO4) filtered and concentrated.The resulting tert-butyl4-[(E)-2-(4-nitrophenyl)ethenyl]piperidine-1-carboxylate was used directly in the nextstep.LC/MS: [(M+1)]+ = 333.

References: [1]Patent: WO2013/39802,2013,A1 .Location in patent: Page/Page column 27.
[2]Patent: EP2755656,2016,B1 .Location in patent: Paragraph 0070.

11
[ 180307-56-6 ]
4-[2-(4-nitrophenyl)ethyl]piperidinium chloride [ No CAS ]

References: [1]Patent: EP2755656,2016,B1 .

12
[ 51376-06-8 ]
[ 180307-56-6 ]
tert-butyl 4-[(E)-2-(2,1,3-benzoxadiazol-5-yl)ethenyl]piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 100℃; for 2h;Inert atmosphere;	[0077] In a 15 mL microwave tube was added <strong>[51376-06-8]5-bromo-2,1,3-benzoxadiazole</strong> (0.94 g, 4.7 mmol), tert-butyl 4-ethenylpiperidine-1-carboxylate (1.0 g, 4.7 mmol), triethylamine (0.66 ml, 4.7 mmol), palladium (II) acetate (0.11 mg, 0.47 mmol)and DMF (5 mL). The solution was degassed and filled with nitrogen (3x), then heated to 100 C for 2 hr. The reactionwas diluted with ethyl acetate, washed with water, filtered through a pad of diatomaceous earth and a plug of silica gel.The organic phase was dried over MgSO4, concentrated and purified by MPLC (eluted with gradient 0->30% EtOAc/Hexane)to provide tert-butyl 4-[(E)-2-(2,1,3-benzoxadiazol-5-yl)ethenyl]piperidine-1-carboxylate as a mixture with the Zolefin.LC-MS (IE, m/z): 352 [M+Na]+.

References: [1]Patent: EP2755656,2016,B1 .Location in patent: Paragraph 0077.

13
[ 1048970-17-7 ]
[ 180307-56-6 ]

References: [1]Organic Letters,2017,vol. 19,p. 2762 - 2765.

14
C₁₈H₃₃BNO₄^(1-)*ClMg⁽¹⁺⁾ [ No CAS ]
[ 180307-56-6 ]

References: [1]Organic Letters,2017,vol. 19,p. 2762 - 2765.

15
[ 180307-56-6 ]
4-(2,2-difluorocyclopropyl)piperidine hydrochloride [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 3126 - 3136.

16
[ 180307-56-6 ]
[ 81290-20-2 ]
tert-butyl 4-(2,2-difluorocyclopropyl)piperidine-1-carboxylate [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 3126 - 3136.

17
[ 180307-56-6 ]
[ 1255208-31-1 ]
[ 1428478-87-8 ]

References: [1]Patent: EP2755656,2016,B1 .
[2]Patent: WO2013/39802,2013,A1 .

18
[ 84358-13-4 ]
[ 180307-56-6 ]

References: [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 13096 - 13100.
Angew. Chem.,2018,vol. 130,p. 13280 - 13284,5.

19
1-(tert-butyl) 4-(1,3-dioxoisoindolin-2-yl) piperidine-1,4-dicarboxylate [ No CAS ]
[ 1119-22-8 ]
[ 180307-56-6 ]

References: [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 13096 - 13100.
Angew. Chem.,2018,vol. 130,p. 13280 - 13284,5.

20
[ 180307-56-6 ]
[ 131738-73-3 ]
C₂₁H₃₁NO₃ [ No CAS ]