Home Cart Sign in  
Chemical Structure| 130368-98-8 Chemical Structure| 130368-98-8

Structure of 130368-98-8

Chemical Structure| 130368-98-8

Benzyl (3-methylenecyclobutyl)carbamate

CAS No.: 130368-98-8

4.5 *For Research Use Only !

Cat. No.: A139567 Purity: 95+%

Change View

Size Price

US Stock

Global Stock

In Stock
50mg łďď¶ÊÊ Inquiry 1-2 weeks
100mg łÇǧ¶ÊÊ Inquiry 1-2 weeks
250mg łÇò˶ÊÊ Inquiry 1-2 weeks
1g łÍ§Ç¶ÊÊ Inquiry 1-2 weeks

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • 50mg

    łďď¶ÊÊ

  • 100mg

    łÇǧ¶ÊÊ

  • 250mg

    łÇò˶ÊÊ

  • 1g

    łÍ§Ç¶ÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 130368-98-8 ]

CAS No. :130368-98-8
Formula : C13H15NO2
M.W : 217.26
SMILES Code : O=C(OCC1=CC=CC=C1)NC2CC(C2)=C
MDL No. :MFCD13192571

Safety of [ 130368-98-8 ]

Application In Synthesis of [ 130368-98-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 130368-98-8 ]

[ 130368-98-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 15760-36-8 ]
  • [ 100-51-6 ]
  • [ 130368-98-8 ]
YieldReaction ConditionsOperation in experiment
66.3% Triethylamine (0.932 mL, 6.69 mmol) was added to a solution of 3- methylenecyclobutanecarboxylic acid (0.5 g, 4.46 mmol) in a mixture of acetonitrile (4.5 mL) and 1 ,4-dioxane (1 .5 mL) at 27 C. Then, diphenyl phosphorazidate (1 .227 mL, 5.35 mmol) was added and the reaction mixture was heated at 75 C for one hour. Then, benzyl alcohol (5 mL, 48.1 mmol) was added at the same temperature. The resultant reaction mixture was stirred at 100 C for sixteen hours. On completion, the reaction mixture was concentrated under reduced pressure to give an impure material. This material was purified via silica gel column chromatography, eluting with ethyl acetate:petroleum ether (3:1 ) to afford benzyl (3- methylenecyclobutyl)carbamate (650 mg, 2.96 mmol, 66.3% yield) as an off white solid. 1H NMR (400 MHz, CDCI3) δ 2.49-2.65 (m, 2 H), 3.01 -3.05 (m, 2 H), 4.16-4.33 (m, 1 H), 4.80-4.89 (m, 2 H), 4.95-5.02 (m, 1 H), 5.10 (s, 2 H), 7.29-7.45 (m, 5 H); LC-MS (LC-ES) M+H = 218.
Diphenylphosphoryl azide (25.3 g, 89 mmol) was added to 3-methylene cyclobutyl carboxylic acid (10 g, 89 mmol) and NEt3 (15 mL, 105 mmol) dissolved in dioxane/MeCN (15mL/35 mL) over 15 minutes. The temperature of the reaction mixture then increased to 75 C with the evolution of gas. After heating the reaction mixture for a further 1 hour at 100 C, benzyl alcohol (20 mL) was added and the reaction mixture was then stirred for 19 hours at 100 C. After cooling and evaporation of the solvent, the residue was taken up in AcOEt (250 mL) and extracted with half cone. NH4CI solution (80 mL), half con. NaHC03 solution (80 mL), and brine (40 mL), dried (MgS04), and concentrated under vacuum. The residue was purified by means of a 120 g RediSept silica gel column using a Sepacore Control chromatographic separator (Biichi) (eluent: hexane/AcOEt = 1 :9 to 4:6) to give the title compound as a white solid. MS (Method L) M+H = 218. HPLC (Method B): tR 3.12 minutes. TLC (AcOEt/hexane = 1 :4): RF = 0.30. 1H-NMR (400 MHz, DMSO-d6): δ ppm 7.64 (d, 1H), 7.32 (m, 5H), 4.99 (s, 2H), 4.76 (s, 2H), 3.95 (sextet, 1 H), 2.85 (m, 2H), 2.62 (m, 2H).
Step Q and R.5: (3-Methylene-cyclobutyl)-carbamic acid benzyl esterDiphenylphosphoryl azide (25.3 g, 89 mmol) was added to 3-methylene cyclobutyl carboxylic acid (10 g, 89 mmol) and NEt3 (15 mL, 105 mmol) dissolved in dioxane/MeCN (15mL/35 mL) over 15 minutes. The temperature of the reaction mixture then increased to 75 C with the evolution of gas. After heating the reaction mixture for a further 1 hour at 100 C, benzyl al- cohol (20 mL) was added and the reaction mixture was then stirred for 19 hours at 100 C. After cooling and evaporation of the solvent, the residue was taken up in AcOEt (250 mL) and extracted with half cone. NH4CI solution (80 mL), half con. NaHC03 solution (80 mL), and brine (40 mL), dried (MgS04), and concentrated under vacuum. The residue was purified by means of a 120 g RediSept silica gel column using a Sepacore Control chromatographic separator (Biichi) (eluent: hexane/AcOEt = 1 :9 -» 4:6) to give the title compound as a white solid. MS (Method L) M+H = 218. HPLC (Method B): tR 3.12 minutes. TLC (AcOEt/hexane = 1 :4): RF = 0.30. 1H-NMR (400 MHz, DMSO-d6): δ ppm 7.64 (d, 1 H), 7.32 (m, 5H), 4.99 (s, 2H), 4.76 (s, 2H), 3.95 (sextet, 1 H), 2.85 (m, 2H), 2.62 (m, 2H).
Diphenylphosphoryl azide (25.3 g, 89 mmol) was added to 3-methylene cyclobutyl carboxylic acid (10 g, 89 mmol) and NEt3 (15 mL, 105 mmol) dissolved in dioxane/MeCN (15mL/35 mL) over 15 minutes. The temperature of the reaction mixture then increased to 75 C with the evolution of gas. After heating the reaction mixture for a further 1 hour at 100 C, benzyl alcohol (20 mL) was added and the reaction mixture was then stirred for 19 hours at 100 C. After cooling and evaporation of the solvent, the residue was taken up in AcOEt (250 mL) and extracted with half cone. NH CI solution (80 mL), half con. NaHC03 solution (80 mL), and brine (40 mL), dried (MgS0 ), and concentrated under vacuum. The residue was purified by means of a 120 g RediSept silica gel column using a Sepacore Control chromatographic separator (Buchi) (eluent: hexane/AcOEt = 1 :9 to 4:6) to give the title compound as a white solid. MS (Method L) M+H = 218. HPLC (Method B): tR 3.12 minutes. TLC (AcOEt/hexane = 1 :4): RF = 0.30. H-NMR (400 MHz, DMSO-d6): 5ppm 7.64 (d, 1 H), 7.32 (m, 5H), 4.99 (s, 2H), 4.76 (s, 2H), 3.95 (sextet, 1 H), 2.85 (m, 2H), 2.62 (m, 2H).
1.2 g Example 73 benzyl (3-methylidene cyclobutyl)carbamate 3-methylidene cyclobutane carboxylic acid (CAS registration No.: 15760-36-8) (1.0 g) and triethylamine (1.6 mL) were dissolved in a mixed solution of 1,4-dioxane (2 mL) and acetonitrile (4 mL), and diphenylphosphoryl azide (1.9 mL) was added thereto. The resulting mixture was stirred at room temperature for 15 minutes. Then, the temperature of the reaction solution was gradually increased to 75C while stirring the reaction solution. After generation of gas (nitrogen) was checked, and the temperature of the reaction solution was increased to 100C. Benzyl alcohol (2.0 mL) was added to the reaction mixture, and the mixture was stirred for 19 hours. The temperature of the reaction solution was returned to room temperature by cooling. Then, the solvent was distilled off by concentration under reduced pressure. Ethyl acetate was added to the obtained residue. The residue was washed with a saturated aqueous solution of ammonium chloride, a saturated aqueous solution of sodium hydrogen carbonate, and a saturated saline solution, sequentially in this order, dried over sodium sulfate, and filtered, followed by concentration under reduced pressure. The obtained residue was purified by column chromatography on silica gel (hexane : ethyl acetate = 100:0 → 30:70) to obtain the title compound (1.2 g) having the following physical property values. 1H-NMR (CDCl3): δ 2.57-2.63, 2.99-3.04, 4.19-4.22, 4.83-4.85, 5.09, 7.26-7.36.

 

Historical Records

Technical Information

Categories