134441-61-5|(R)-N-Boc-Piperidine-2-methanol| Ambeed

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Quality Control of [ 134441-61-5 ] Purity: 95% SDS Specification

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Product Details of [ 134441-61-5 ]

CAS No. :	134441-61-5
Formula :	C₁₁H₂₁NO₃
M.W :	215.29
SMILES Code :	C(=O)(OC(C)(C)C)N1CCCC[C@@H]1CO
MDL No. :	MFCD04973120
InChI Key :	PZTAGFCBNDBBFZ-SECBINFHSA-N
Pubchem ID :	6933953

Safety of [ 134441-61-5 ]

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

Computational Chemistry of [ 134441-61-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	0
Fraction Csp3	0.91
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	62.56
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	49.77 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.74
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	1.34
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.39
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.	1.15
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	0.93
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.51

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.75
Solubility	3.78 mg/ml ; 0.0176 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	2.22 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	-1.11
Solubility	16.7 mg/ml ; 0.0774 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.	-6.66 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	0.0 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)	2.74

Application In Synthesis of [ 134441-61-5 ]

* 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 [ 134441-61-5 ]
Downstream synthetic route of [ 134441-61-5 ]

[ 134441-61-5 ] Synthesis Path-Upstream 1~1

1
[ 134441-61-5 ]
[ 688809-99-6 ]

References: [1] Patent: WO2012/117048, 2012, A1, .

[ 134441-61-5 ] Synthesis Path-Downstream 1~35

1
[ 28697-17-8 ]
[ 134441-61-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With borane-THF; at 0 - 20℃; for 2h;	Compound 2a (5.0 g, 21.8 mmol, 1.0 eq) was dissolved in THF (60 mL),The temperature of the reaction system was lowered to 0 C, BH3.THF (26.2 ml, 26.2 mmol, 1.2 eq) was added to the reaction system, and the temperature was raised to room temperature and stirred for 2 h.The reaction was quenched with saturated NaHCO3 and extracted with EtOAc (2 x 30 mL).It was washed with saturated brine, dried over Na2SO4, and spin-dried to obtain compound 2b (4.8 g, yield: 100%).TLC: DCM / MeOH = 10/1, I2, Rf (compound 2a) = 0.2, Rf (compound 2b) = 0.4.
99%		EXAMPLE 50(b); Starting Material for Examples 50 Et Seq; Step 1; (R)-2-Hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester; To a solution of (R)-Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (5 g, 21.8 mmol) in anhydrous THF (32 mL) at 0-5 C. was added borane-tetrahydrofuran complex (1M solution in THF) (3.6 g, 41.84 mmol) over a period of 15 min. The mixture was stirred at 0-5 C. for 2 h and then at it for 2 h. The mixture was added over a period of 10 min to cold water (75 mL) and extracted with EtOAc (300 mL). The aqueous layer was re-extracted with EtOAc (2×150 mL). The organic layers were combined, dried over anhydrous Na2SO4 and concentrated to obtain the title product as a colorless oil (4.65 g., 99%).
82%	With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃; for 18.25h;	A solution of (R)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (Example 15g,18.5 g, 80.7 mmol) in anhydrous THF (44.4 mL) was cooled to 0C. BH3"Me2S (44.4 mL,88.8 mmol) was added drop wise over 15 minutes. After complete addition, the mixture wasallowed to warm to room temperature, and stirring was continued for 18 hours. The mixturewas quenched with water, and extracted with ethyl acetate. The organic extract was dried15 over anhydrous Na2S04, filtered, and concentrated. The resulting residue was flashchromatographed on silica gel (35% ethyl acetate in hexanes) to provide (R)-tert-butyl-2-(hydroxymethyl)piperidine-1-carboxylate as a white solid (14.2 g, 82%). MS 116 (MH+boc)

References: [1]Patent: CN110590747,2019,A .Location in patent: Paragraph 0292-0294.
[2]Patent: US2007/66820,2007,A1 .Location in patent: Page/Page column 41.
[3]Organic Letters,2004,vol. 6,p. 1813 - 1816.
[4]Journal of Medicinal Chemistry,1992,vol. 35,p. 1550 - 1557.
[5]Patent: WO2014/25706,2014,A1 .Location in patent: Page/Page column 73.

2
[ 134441-61-5 ]
[ 134526-69-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 2h;	Dess-Matin (10.4 g, 24.5 mmol, 1.1 eq) was added to compound 2b (4.8 g, 22.3 mmol, 1.0 eq) in DCM (60 mL).Reaction at room temperature for 2h.The reaction was poured into saturated NaHCO3 and extracted with EtOAc (2 x 30 mL).The organic phases were combined, washed with saturated brine, dried over Na2SO4, spin-dried, and passed through a column (PE / EA = 8/1) to obtain compound 2 (3.9 g, yield: 82%).TLC: PE / EA = 2/1, I2, Rf (compound 2b) = 0.2, Rf (compound 2) = 0.4.

References: [1]Patent: CN110590747,2019,A .Location in patent: Paragraph 0294; 0296-0298.
[2]Organic Letters,2004,vol. 6,p. 1813 - 1816.
[3]Journal of Medicinal Chemistry,1992,vol. 35,p. 1550 - 1557.
[4]Journal of the American Chemical Society,1999,vol. 121,p. 700 - 709.

3
[ 134441-61-5 ]
[ 28697-17-8 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 237 - 240.

4
[ 134441-61-5 ]
[ 708260-80-4 ]

References: [1]Organic Letters,2004,vol. 6,p. 1813 - 1816.

5
[ 134441-61-5 ]
[ 708260-84-8 ]

References: [1]Organic Letters,2004,vol. 6,p. 1813 - 1816.

6
[ 134441-61-5 ]
tert-butyl (2R)-2-[(1S)-1-acryloyloxy-1-[2-(1,3-dioxolan-2-yl)ethyl]-2-propenyl]piperidine-1-carboxylate [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 1813 - 1816.

7
[ 134441-61-5 ]
tert-butyl (2R)-2-[(1R)-1-acryloyloxy-1-[2-(1,3-dioxolan-2-yl)ethyl]-2-propenyl]piperidine-1-carboxylate [ No CAS ]

References: [1]Organic Letters,2004,vol. 6,p. 1813 - 1816.

8
[ 4043-87-2 ]
[ 134441-61-5 ]

References: [1]Tetrahedron Asymmetry,2003,vol. 14,p. 1685 - 1689.

9
[ 596129-25-8 ]
[ 134441-61-5 ]

References: [1]Tetrahedron Asymmetry,2003,vol. 14,p. 1685 - 1689.

10
[ 1723-00-8 ]
[ 134441-61-5 ]

References: [1]Journal of the American Chemical Society,1999,vol. 121,p. 700 - 709.
[2]Journal of Organic Chemistry,1997,vol. 62,p. 5023 - 5033.
[3]Journal of the American Chemical Society,1995,vol. 117,p. 9369 - 9370.
[4]Journal of Medicinal Chemistry,1992,vol. 35,p. 1550 - 1557.
[5]Patent: WO2012/117048,2012,A1 .
[6]Patent: WO2014/25706,2014,A1 .

11
[ 134441-61-5 ]
[ 6879-74-9 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5023 - 5033.
[2]Journal of the American Chemical Society,1995,vol. 117,p. 9369 - 9370.

12
[ 134441-61-5 ]
[ 168610-12-6 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5023 - 5033.
[2]Journal of the American Chemical Society,1995,vol. 117,p. 9369 - 9370.

13
[ 134441-61-5 ]
[ 168610-13-7 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5023 - 5033.
[2]Journal of the American Chemical Society,1995,vol. 117,p. 9369 - 9370.

14
[ 134441-61-5 ]
[ 168417-04-7 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5023 - 5033.
[2]Journal of the American Chemical Society,1995,vol. 117,p. 9369 - 9370.

15
[ 134441-61-5 ]
[ 518-99-0 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5023 - 5033.
[2]Journal of the American Chemical Society,1995,vol. 117,p. 9369 - 9370.

16
[ 134441-61-5 ]
[ 168417-07-0 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5023 - 5033.
[2]Journal of the American Chemical Society,1995,vol. 117,p. 9369 - 9370.

17
[ 134441-61-5 ]
[ 192133-54-3 ]