tert-butyl 4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate Chemical Properties

Melting point:

85 °C

Boiling point:

354℃

Density 

1.129

Flash point:

168℃

storage temp. 

2-8°C

form 

powder to crystal

pka

-1.46±0.20(Predicted)

color 

White to Almost white

InChI

InChI=1S/C14H23NO4/c1-5-18-12(16)10-11-6-8-15(9-7-11)13(17)19-14(2,3)4/h10H,5-9H2,1-4H3

InChIKey

NJORMFNJZLXLCN-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CC/C(=C\C(OCC)=O)/CC1

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

tert-butyl 4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate Usage And Synthesis

Synthesis

The general procedure for the synthesis of tert-butyl 4-(2-ethoxy-2-oxo-substituted)piperidine-1-carboxylate from triethyl phosphonoacetate and N-tert-butoxycarbonyl-4-piperidone was as follows: to a solution of tetrahydrofuran (200 mL) of ethyl diethylphosphonoacetate (28.3 g) was added 60% sodium hydride (4.82 g). The mixture was stirred under cooling in an ice bath for 30 min, followed by the slow dropwise addition of a tetrahydrofuran (200 mL) solution of N-tert-butoxycarbonyl-4-piperidone (20 g). The reaction mixture was stirred continuously for 22 h at room temperature. Upon completion of the reaction, the reaction was terminated by the addition of water (200 mL) and extracted with ethyl acetate. The organic phases were combined and washed with saturated aqueous sodium chloride solution and subsequently dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the crude product was purified by silica gel column chromatography using hexane/ethyl acetate (6:1) as eluent to finally obtain tert-butyl 4-(2-ethoxy-2-oxo-substituted)piperidine-1-carboxylate (27.3 g, 100% yield) as a colorless powder. The product was characterized by 1H NMR (CDCl3): δ 1.28 (3H, t, J = 7.4 Hz), 1.47 (9H, s), 2.24-2.33 (2H, m), 2.90-2.98 (2H, m), 3.43-3.55 (4H, m), 4.16 (2H, q, J = 7.4 Hz), 5.70-5.73 (1H, m ).

References

[1] Heterocycles, 2001, vol. 54, # 2, p. 747 - 755
[2] Patent: EP1498125, 2005, A1. Location in patent: Page/Page column 84-85
[3] Patent: WO2018/152329, 2018, A1. Location in patent: Page/Page column 48
[4] Patent: CN102952072, 2016, B. Location in patent: Paragraph 0109
[5] Chinese Chemical Letters, 2012, vol. 23, # 6, p. 707 - 710

tert-butyl 4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate(135716-08-4)Related Product Information

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