BENZYL 3-OXOCYCLOBUTYLCARBAMATE Chemical Properties

Boiling point:

403.3±44.0 °C(Predicted)

Density 

1.22

storage temp. 

2-8°C

pka

11.39±0.20(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C12H13NO3/c14-11-6-10(7-11)13-12(15)16-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,13,15)

InChIKey

PSAMWNBBHLUISE-UHFFFAOYSA-N

SMILES

C(OCC1=CC=CC=C1)(=O)NC1CC(=O)C1

Safety Information

HS Code 

2922498590

BENZYL 3-OXOCYCLOBUTYLCARBAMATE Usage And Synthesis

Uses

Benzyl 3-Oxocyclobutylcarbamate is used in process for preparation of abrocitinib.

Synthesis

3-Oxocyclobutanecarboxylic acid (1.0 g, 8.77 mmol) and benzyl alcohol (1.14 g, 10.52 mmol) were used as raw materials, and 3-oxocyclobutanecarboxylic acid was mixed with DIEA (1.92 g, 14.92 mmol) and DPPA (2.89 g, 10.52 mmol) in toluene (8 mL) under argon protection. The reaction mixture was heated to 60 °C and maintained for 3 h. Benzyl alcohol was then added. Stirring was continued at 60 °C overnight. Upon completion of the reaction, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 8:1) to afford the target product benzyl 3-oxocyclobutylcarbamate (240 mg, 50% yield). The product was characterized by 1H NMR (500 MHz, CDCl3) and ESI-MS: 1H NMR δ 7.38-7.33 (m, 5H), 5.12 (d, J = 7.5 Hz, 2H), 4.34-4.33 (brs, 1H), 3.44-3.39 (m, 2H), 3.10-3.07 (brs, 2H) ppm; ESI-MS (m/z): 220.2 [M + 1]+.

References

[1] Patent: WO2012/75381, 2012, A1. Location in patent: Page/Page column 210
[2] Patent: WO2012/9678, 2012, A1. Location in patent: Page/Page column 210
[3] Patent: EP1256578, 2002, A1. Location in patent: Page 22
[4] Patent: WO2014/74421, 2014, A1. Location in patent: Page/Page column 56; 57

BENZYL 3-OXOCYCLOBUTYLCARBAMATE(130369-36-7)Related Product Information

• ETHYL 3-OXO CYCLOBUATNE CARBOXYLATE
• 3-Oxocyclobutanecarboxylic acid
• Cyclobutanone
• CYCLOBUTYLHYDRAZINE DIHYDROCHLORIDE
• 1-CYCLOBUTYLHYDRAZINE HYDROCHLORIDE
• N-Boc-1-aminocyclobutanecarboxylic acid
• Carbamic acid, (3-hydroxycyclobutyl)-, 1,1-dimethylethyl ester (9CI)
• 3-PHENYL-CYCLOBUTAN-1-ONE
• 3-Methylenecyclobutanecarbonitrile
• Cyclobutylmethylamine hydrochloride
• 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
• 2-AMINO-3-BROMOPHENOL
• 3-IODO-4-METHOXY-5-AZAINDOLE
• 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone
• 4,5-DICHLOROPHTHALIC ACID
• 1H-Pyrrolo[3,2-c]pyridine-3-carboxylic acid, 6-bromo-
• 6-CHLORO-5-AZAINDOLE
• (3-BroMo-pyridin-2-yl)-acetic acid ethyl ester