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ChemicalBook--->CAS DataBase List--->74892-82-3

74892-82-3

74892-82-3 Structure

74892-82-3 Structure
IdentificationMore
[Name]

Ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate
[CAS]

74892-82-3
[Synonyms]

(2R,4R)-4-METHYL-2-PIPERIDINECARBOXYLATE
ethyl (2r,4r)-4-methyl-2-piperidinecarboxylate
(2R,4R)4-methylpiperidecarboxylicacid
(2R,4R)-ETHYL 4-METHYLPIPERIDINE-2-CARBOXYLATE
(2R,4R)-4-Methylpipecolinic acid
[EINECS(EC#)]

1806241-263-5
[Molecular Formula]

C9H17NO2
[MDL Number]

MFCD03839858
[Molecular Weight]

171.24
[MOL File]

74892-82-3.mol
Chemical PropertiesBack Directory
[Boiling point ]

226.1±33.0 °C(Predicted)
[density ]

0.969±0.06 g/cm3(Predicted)
[storage temp. ]

Keep in dark place,Sealed in dry,Store in freezer, under -20°C
[solubility ]

Chloroform (Sparingly), Ethanol (Slightly), Methanol (Soluble)
[form ]

Oil
[pka]

6.65±0.10(Predicted)
[color ]

Light Yellow to Yellow
[InChI]

InChI=1S/C9H17NO2/c1-3-12-9(11)8-6-7(2)4-5-10-8/h7-8,10H,3-6H2,1-2H3/t7-,8-/m1/s1
[InChIKey]

GHBNOCBWSUHAAA-HTQZYQBOSA-N
[SMILES]

N1CC[C@@H](C)C[C@@H]1C(OCC)=O
[CAS DataBase Reference]

74892-82-3(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H227-H315-H319-H335
[Precautionary statements ]

P305+P351+P338
[HS Code ]

29333990
Hazard InformationBack Directory
[Chemical Properties]

light yellow solution
[Uses]

Ethyl (2R,4R)-4-Methylpipecolate is an intermediate in the preparation of Argatroban (A769000).
[Synthesis]

2-Piperidinecarboxylic acid, 4-methyl-1-[(1S)-1-phenylethyl]-, ethyl ester, (2R,4R)-

198641-56-4

Ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate

74892-82-3

General procedure for the synthesis of ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate from the compound (CAS: 198641-56-4): (1'S,2R,4R)-6 (2.5 g, 9 mmol) was dissolved in ethanol (120 mL) and 10% Pd(OH)2/C (0.27 g) was added. The hydrogenation reaction was carried out at room temperature and at atmospheric pressure. The reaction progress was monitored by TLC (unfolding agent: chloroform/methanol, 9:1). After 4 hours of reaction, the catalyst was removed by filtration through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (silica gel to sample mass ratio 1:20) to afford pure ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate (0.7 g, 45% yield) using dichloromethane/methanol (98:2) as eluent. The product was characterized by 1H NMR (CDCl3): δ 0.96 (d, 3H, J = 6.50 Hz, CH3-4); 1.15 (m, 1H, H-5a); 1.32 (t, 3H, J = 7.2 Hz, CH3CH2); 1.42-1.54 (m, 1H, H-3); 1.5-1.69 (m, 2H, H-4, H-5b) ; 2.00-2.11 (m, 2H, H-3b and NH); 2.87 (m, 2H, H-6); 3.65 (m, 1H, H-2); 4.21 (q, 2H, J = 7.2 Hz, CH2CH3). Specific optical rotation [α]20D = -22 (c 5, ethanol) (enantiomeric excess value e.e. = +24).

[References]

[1] Tetrahedron Asymmetry, 2011, vol. 22, # 16-17, p. 1626 - 1631
[2] Patent: CN107043347, 2017, A. Location in patent: Paragraph 0029; 0030; 0031; 0032-0034; 0039-0044; 0046; 0048
Spectrum DetailBack Directory
[Spectrum Detail]

Ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate(74892-82-3)1HNMR
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