140645-24-5|tert-Butyl (S)-3-(aminomethyl)piperidine-1-carboxylate| Ambeed

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Quality Control of [ 140645-24-5 ] Purity: 98% SDS Specification

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Product Details of [ 140645-24-5 ]

CAS No. :	140645-24-5
Formula :	C₁₁H₂₂N₂O₂
M.W :	214.30
SMILES Code :	C(=O)(OC(C)(C)C)N1CCC[C@H](C1)CN
MDL No. :	MFCD03839877
InChI Key :	WPWXYQIMXTUMJB-VIFPVBQESA-N
Pubchem ID :	1502022

Safety of [ 140645-24-5 ]

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

Application In Synthesis of [ 140645-24-5 ]

* 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.

Downstream synthetic route of [ 140645-24-5 ]

[ 140645-24-5 ] Synthesis Path-Downstream 1~35

1
[ 501-53-1 ]
[ 140645-24-5 ]
[ 140645-87-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine; In dichloromethane; at 0℃; for 16h;	(»S)-fert-Butyl 3-(aminomethyl)piperidine-l-carboxylate (1.00 g, 4.67 mmol) wasdissolved in 14 mL anhydrous CH2CI2 under an N2 atmosphere and cooled to 0 C. Triethylamine (1.30 mL, 945 mg, 9.34 mmol) was added followed by the dropwise addition of benzyl chloroformate (0.99 mL, 1.20 g, 7.00 mmol). After 16 h, the reaction mixture was partitioned between H2O and CH2Cl2,and separated, and the aqueous layer was extracted twice with CH2CI2. The organic layers were combined, dried over Na2SC>4, filtered, and concentrated to a light yellow oil. Purification via silica gel chromatography using 97% CH2Cl2/3% MeOH gave benzyl ((S)- l-(tert-butoxycarbonyl)piperidin-3-yl)methylcarbamate as a clear colorless oil (895 mg, 55%). LC/MS: m/z 349.5 (M+H)+ at 3.21 min (10%-99% CH3CN (0.035% TFA)/H20 (0.05% TFA)).

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3889 - 3901.
[2]Patent: WO2006/28904,2006,A1 .Location in patent: Page/Page column 248.
[3]Patent: WO2004/35569,2004,A2 .Location in patent: Page/Page column 25-26.

2
[ 155541-67-6 ]
[ 140645-24-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 437 - 440.
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 3889 - 3901.
[3]Patent: WO2004/35569,2004,A2 .Location in patent: Page/Page column 24-25.

3
[ 140645-24-5 ]
[ 382637-78-7 ]
[ 847831-94-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 787 - 791.

4
[ 140645-24-5 ]
[ 675122-49-3 ]
[ 676622-21-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 21h;	Part A. Preparation of (S)-3-{3-[3-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-ureidomethyl}-piperidine-1-carboxylic Acid Tert-butyl Ester Racemic 3-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester was resolved using the procedure of B. Wirz and W. Walther, Tetrahedron Asymm. 1992, 3, 1049. The (R) isomer was converted into (S)-3-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester by the method of K. Hilpert et al., J. Med. Chem. 1994, 37, 3889. A solution of this material (119 mg, 556 mumol) in N,N-dimethylformamide (4 mL) was treated with [3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-carbamic acid phenyl ester (180 mg, 556 mumol) and triethylamine (155 muL, 1.11 mmol) and the mixture was stirred at room temperature for 21 hours. The mixture was concentrated under vacuum, and the residue was dissolved in dichloromethane. The solution was washed with 1.0 N aqueous sodium hydroxide, dried over sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography, elution with 70% ethyl acetate in hexane, to provide a white glassy solid (193 mg, 78%). 1H NMR (300 MHz, CDCl3) delta 7.64 (s, 1H), 7.55 (s, 1H), 7.18 (s, 1H), 4.20 (s, 3H), 3.9-3.6 (m, 3H), 3.28 (m, 1H), 3.05 (m, 2H), 1.83 (m, 1H), 2.66 (q, J=8 Hz, 2H), 1.9-1.5 (m, 5H), 1.46 (s, 9H), 1.24 (t, J=8 Hz, 3H).

References: [1]Patent: US2004/67935,2004,A1 .Location in patent: Page/Page column 36-37.
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 787 - 791.

5
[ 57372-27-7 ]
[ 140645-24-5 ]
3-[(2-naphthalen-2-yl-thiazole-4-carbonyl)-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]