(1r,4r)-methyl 4-(hydroxymethyl)cyclohexanecarboxylate Chemical Properties

Boiling point:

251℃

Density 

1.058

Flash point:

57℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)

form 

Oil

pka

15.05±0.10(Predicted)

color 

Colourless

InChI

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

InChIKey

KOGYKIDJFOMAOF-ZKCHVHJHSA-N

SMILES

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

Safety Information

HS Code 

2918199890

(1r,4r)-methyl 4-(hydroxymethyl)cyclohexanecarboxylate Usage And Synthesis

Uses

Methyl 4-(Hydroxymethyl)cyclohexanecarboxylate is a useful reagent in the synthesis and biopharmaceutical evaluation of imatinib analogs.

Synthesis

Tetrahydrofuran (100 mL) was cooled to -14 °C under argon protection and a tetrahydrofuran solution (100 mL) of 1.0 M borane-tetrahydrofuran complex was slowly added. Subsequently, a tetrahydrofuran solution (78 mL) of monomethyl trans-1,4-cyclohexanedicarboxylate (14.3 g) was added dropwise to this solution, and the dropwise acceleration was controlled so that the reaction was completed within 1 hour. The reaction mixture was warmed to 50 °C and stirring was continued at -10 °C for 1 hour. Upon completion of the reaction, water (160 mL) and saturated aqueous sodium bicarbonate solution (160 mL) were sequentially added to the reaction mixture under cooling in an ice bath, followed by extraction with ethyl acetate (160 mL x 4). The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product obtained was purified by fast column chromatography on silica gel (eluent: chloroform/methanol=20:1) to give methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (13.25 g, yield: 100%) as an oil. Mass spectrum (APCI) m/z: 173 [M+H]+.

References

[1] Patent: EP1772454, 2007, A1. Location in patent: Page/Page column 55
[2] Patent: US2014/221350, 2014, A1. Location in patent: Paragraph 0166
[3] Patent: CN105566324, 2016, A. Location in patent: Paragraph 0394; 0395; 0396; 0397
[4] Patent: WO2013/192088, 2013, A1. Location in patent: Paragraph 00215

(1r,4r)-methyl 4-(hydroxymethyl)cyclohexanecarboxylate(110928-44-4)Related Product Information

• BOC-1,4-TRANS-ACHC-OH
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