Methyl cis-3-hydroxycyclobutanecarboxylate Chemical Properties

Boiling point:

190℃

Density 

1.232

Flash point:

76℃

storage temp. 

2-8°C

pka

14.73±0.40(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C6H10O3/c1-9-6(8)4-2-5(7)3-4/h4-5,7H,2-3H2,1H3/t4-,5+

InChIKey

BYKHAEUVLSBWSU-SYDPRGILSA-N

SMILES

[C@@H]1(C(OC)=O)C[C@H](O)C1

Safety Information

HS Code 

2918999090

Methyl cis-3-hydroxycyclobutanecarboxylate Usage And Synthesis

Synthesis

Methyl 3-oxocyclobutanecarboxylate (3075 g, 24.0 mol, 1.0 eq.) was dissolved in 30 L of tetrahydrofuran and cooled to -78 to -60 °C. Under stirring, 20 L of tetrahydrofuran solution of lithium hydrogenated tri-tert-butoxyaluminum (36.0 mol, 1.5 eq.) was added dropwise and the reaction was kept for 4 hours. Upon completion of the reaction, the progress of the reaction was monitored by TLC. Subsequently, the reaction was quenched dropwise by addition of 6 mol/L hydrochloric acid and the pH of the reaction solution was adjusted to 5-6 at about 0 °C. The reaction mixture was diluted with 20 L of ethyl acetate and stirred for 30 min. The reaction mixture was filtered through a diatomaceous earth pad and the filter cake was washed three times with ethyl acetate. The filtrate was separated and the aqueous phase was extracted and washed with ethyl acetate. All organic phases were combined and concentrated by drying to give methyl cis-3-hydroxycyclobutanecarboxylate (2733 g, 21.0 mol) in light yellow liquid form in 88% yield and 95% purity.

References

[1] Patent: CN108129288, 2018, A. Location in patent: Paragraph 0047; 0048; 0052
[2] Patent: WO2015/181186, 2015, A1. Location in patent: Page/Page column 149

Methyl cis-3-hydroxycyclobutanecarboxylate(63485-50-7)Related Product Information

• cis-3-aMinocyclohexane carboxylic acid Methyl ester*HCl
• tert-butyl (2R,6S)-2,6-dimethylpiperazine-1-carboxylate
• cis-3,4-dimethoxypyrrolidine hydrochloride
• cis-3,4-Dihydroxypyrrolid...
• cis-3-MethoxycyclobutanaMine hydrochloride
• cis-3-Hydroxycyclobutanecarboxylic acid
• cis-tert-Butyl 3-hydroxy-3-MethylcyclobutylcarbaMate
• Cyclobutanecarboxylic acid, 3-hydroxy-1-methyl-, methyl ester, cis- (9CI)
• cis-tert-butyl 3-hydroxycyclobutanecarboxylate
• TERT-BUTYL CIS-3-HYDROXYMETHYLCYCLOBUTYLCARBAMATE
• cis-3-amino-1-methylcyclobutan-1-ol hydrochloride
• (1s,3s)-methyl 3-aminocyclobutane carboxylate hydrochloride
• Cis Methyl 3-aMinocyclopentanecarboxylate hydrochloride
• cis-4-(MethylaMino)cyclohexanol hydrochloride
• cis-Ethyl 4-aMinocyclohexanecarboxylate hydrochloride
• Cyclopentanecarboxylic acid, 3-amino-, (1R,3S)-rel- (9CI)
• (cis)-3-Hydroxy-cyclopentanecarboxylic ac id Methyl ester
• Benzyl cis-3-hydroxycyclobutanecarboxylate