| Identification | Back Directory | [Name]
Ethyl N-Boc-4-methylpiperidine-4-carboxylate | [CAS]
189442-87-3 | [Synonyms]
ETHYL N-BOC-4-METHYLPIPERIDINE-4-CARBOX&
Ethyl 1-Boc-4-methylpiperidine-4-carboxylate
N-BOC-4-METHYL ISONIPECOTIC ACID ETHYL ESTER
N-BOC-4-METHYL-4-METHYLPIPERIDINECARBOXYLATE
ETHYL N-BOC-4-METHYLPIPERIDINE-4-CARBOXYLATE
1-Boc-4-Methyl-isonipecotic acid ethyl ester
ETHYL 1-N-BOC-4-METHYL-PIPERIDINE-CARBOXYLATE
N-Boc-4-Methyl isonipecotic acid ethyl ester ,95%
Ethyl N-Boc-4-methylpiperidine-4-carboxylate ,97%
1,4-PIPERIDINEDICARBOXYLIC ACID, 4-1-(1,1-DIMETHYL
Ethyl N-Boc-4-methylpiperidine-4-carboxylate USP/EP/BP
1-tert-butyl 4-ethyl 4-Methylpiperidine-1,4-dicarboxylate
1-TERT-BUTYL 4-METHYL 4- METHYLPIPERIDINE1,4-DICARBOXYLATE
1-O-TERT-BUTYL 4-O-ETHYL 4-METHYLPIPERIDINE-1,4-DICARBOXYLATE
1-tert-Butoxycarbonyl-4-methylpiperidine-4-carboxylic acid ethyl ester
4-Methyl-1,4-piperidinedicarboxylic acid 1-(1,1-dimethylethyl) 4-ethyl ester
1,4-Piperidinedicarboxylic acid, 4-methyl-, 1-(1,1-dimethylethyl) 4-ethyl ester
N-BOC-4-METHYL-4-METHYLPIPERIDINECARBOXYLATEN-BOC-4-METHYL ISONIPECOTIC ACID ETHYL ESTER | [Molecular Formula]
C14H25NO4 | [MDL Number]
MFCD03411922 | [MOL File]
189442-87-3.mol | [Molecular Weight]
271.35 |
| Chemical Properties | Back Directory | [Boiling point ]
329.7±35.0 °C(Predicted) | [density ]
1.0134 | [refractive index ]
1.4554 | [Fp ]
110 °C | [storage temp. ]
2-8°C | [pka]
-2.20±0.40(Predicted) | [Appearance]
Colorless to light yellow Liquid | [InChI]
1S/C14H25NO4/c1-6-18-11(16)14(5)7-9-15(10-8-14)12(17)19-13(2,3)4/h6-10H2,1-5H3 | [InChIKey]
ZQZVWDXMUCTNRI-UHFFFAOYSA-N | [SMILES]
CCOC(=O)C1(C)CCN(CC1)C(=O)OC(C)(C)C |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
25-37/38-41 | [Safety Statements ]
26-36/37/39-45 | [RIDADR ]
UN 2810 | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
Reactant for synthesis of:
- Dipeptidyl peptidase-4 inhibitor ABT-279
- Building blocks for piperazine-based CCR5 antagonists
| [Synthesis]
Ethyl N-Boc-4-piperidinecarboxylate (10.00 g, 36.92 mmol) was dissolved in tetrahydrofuran (THF, 100 mL) and the solution was cooled to -78 °C. Under nitrogen protection, lithium diisopropylammonium (LDA, 47 mmol, 23 mL) was slowly added, maintaining the temperature at -78 °C, and the reaction mixture was stirred for 1 hour. Subsequently, iodomethane (81.25 mmol, 5.08 mL) was added dropwise and stirring was continued at -78 °C for 1 hour. Upon completion of the reaction, the cold bath was removed and the reaction mixture was allowed to warm slowly to room temperature and stirring was continued for 30 min. The reaction was quenched with saturated ammonium chloride (NH4Cl) solution followed by partition extraction with ethyl acetate (EtOAc). The organic phases were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to afford the target product ethyl N-Boc-4-methyl-4-piperidinecarboxylate in quantitative yield. The product was characterized by 1H NMR (400 MHz, DMSO-d6) with chemical shifts δ: 4.11 (q, J=7.1 Hz, 2H), 3.61 (dt, J=13.4 Hz, J=4.5 Hz, 2H), 2.95 (d, J=0.3 Hz, 2H), 1.91 (d, J=13.6 Hz, 2H), 1.39 (s, 9H) , 1.31 (m, 2H), 1.19 (m, 3H), 1.15 (s, 3H). | [References]
[1] Patent: WO2015/86527, 2015, A1. Location in patent: Page/Page column 113; 114
[2] Patent: WO2015/86525, 2015, A1. Location in patent: Page/Page column 117
[3] Patent: WO2008/121687, 2008, A2. Location in patent: Page/Page column 43; 89; 94
[4] Patent: WO2006/83003, 2006, A1. Location in patent: Page/Page column 36-37
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 11, p. 4680 - 4692 |
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