Ethyl trans-4-Hydroxycyclohexanecarboxylate Chemical Properties

Boiling point:

144°C/12mmHg(lit.)

Density 

1.093±0.06 g/cm3(Predicted)

refractive index 

1.4630 to 1.4670

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

pka

14.98±0.40(Predicted)

color 

Colorless to Almost colorless

InChI

InChI=1S/C9H16O3/c1-2-12-9(11)7-3-5-8(10)6-4-7/h7-8,10H,2-6H2,1H3/t7-,8-

InChIKey

BZKQJSLASWRDNE-ZKCHVHJHSA-N

SMILES

[C@@H]1(C(OCC)=O)CC[C@@H](O)CC1

Safety Information

HS Code 

2918199890

Ethyl trans-4-Hydroxycyclohexanecarboxylate Usage And Synthesis

Uses

trans-Ethyl 4-hydroxycyclohexanecarboxylate acts as a reagent in the discovery of Mer kinase inhibitors for the treatment of pediatric acute lymphoblastic leukemia, in the structural activity relationship study of piperidine-based derivatives as novel influenza virus inhibitors.

Synthesis

To a solution of ethyl 4-oxocyclohexanecarboxylate (13.5 g, 79 mmol) in methanol (150 mL) at 0 °C was slowly added sodium borohydride (5.3 g, 140 mmol). The reaction mixture was stirred continuously for 3 hours at room temperature. Upon completion of the reaction, the reaction was quenched by the addition of water (50 mL) followed by extraction with ethyl acetate (150 mL x 1, 50 mL x 2). The organic phases were combined, washed with water (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent ratio: hexane-ethyl acetate 1.5:1 to 1:1) to afford ethyl trans-4-hydroxycyclohexanecarboxylate (12 g, 88% yield, cis-trans ratio = 3:7) as a colorless transparent oil.1H NMR (300 MHz, CDCl3, cis-trans mixture) δ: 4.17-4.08 (m, 2H), 3.90 ( bs, 0.3H), 3.68-3.57 (m, 0.7H), 2.42-1.28 (m, 9H), 1.27-1.22 (m, 3H) ppm.(Hydroxyl signal was not observed.)

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 8967 - 9004
[2] Organic Process Research and Development, 2010, vol. 14, # 4, p. 883 - 889
[3] Patent: WO2005/80317, 2005, A2. Location in patent: Page/Page column 150
[4] Tetrahedron Letters, 2000, vol. 41, # 39, p. 7567 - 7570
[5] Patent: US5175290, 1992, A

Ethyl trans-4-Hydroxycyclohexanecarboxylate(3618-04-0)Related Product Information

• TRANS-1,4-CYCLOHEXANE DIISOCYANATE
• trans-Methyl-4-aMinocyclohexanecarboxylate
• (R,R)-3,4-TRANS-(N-BOC)-DIAMINOPYRROLIDINE
• 3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester,
• Cyclohexanecarboxylic acid ethyl ester