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

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 Information

HS Code 

29333990

Ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate Usage And Synthesis

Chemical Properties

light yellow solution

Uses

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

Synthesis

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

Ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate(74892-82-3)Related Product Information

• Tribenuron methyl
• Methyl acrylate
• Kresoxim-methyl
• Methanol
• Methyl salicylate
• Methylparaben
• 2,2,6,6-Tetramethylpiperidinooxy
• Basic Violet 1
• Urethane
• Triethyl orthoformate
• Ethyl formate
• 2,2,6,6-Tetramethyl-4-piperidinol
• METSULFURON METHYL
• Ethyl (2R,4R)-1-(Nitroglycerine-nitro-L-arginyl)-4-methyl-piperidinecarboxylate hydrochloride
• (2R,4R)-4-Methylpiperidine-2-carboxylic acid
• 3-Methyl-8-quinolinesulphonyl chloride
• Argatroban
• Methyl