tert-Butyl 3-(4-nitrophenyl)azetidine-1-carboxylate
- Product Name
- tert-Butyl 3-(4-nitrophenyl)azetidine-1-carboxylate
- CAS No.
- 883901-62-0
- Chemical Name
- tert-Butyl 3-(4-nitrophenyl)azetidine-1-carboxylate
- Synonyms
- 1-Boc-3-(4-nitrophenyl)azetidine;tert-Butyl 3-(4-nitrophenyl)azetidine-1-carboxylate;1-Azetidinecarboxylic acid, 3-(4-nitrophenyl)-, 1,1-dimethylethyl ester
- CBNumber
- CB85416880
- Molecular Formula
- C14H18N2O4
- Formula Weight
- 278.3
- MOL File
- 883901-62-0.mol
tert-Butyl 3-(4-nitrophenyl)azetidine-1-carboxylate Property
- storage temp.
- 2-8°C
- Appearance
- Light yellow to yellow Solid
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 5647DN
- Product name
- Tert-Butyl3-(4-nitrophenyl)azetidine-1-carboxylate
- Packaging
- 1g
- Price
- $849
- Updated
- 2021/12/16
- Product number
- CD11373483
- Product name
- tert-Butyl3-(4-nitrophenyl)azetidine-1-carboxylate
- Purity
- 97%
- Packaging
- 5g
- Price
- $1979
- Updated
- 2021/12/16
- Product number
- AY16298
- Product name
- 1-Azetidinecarboxylicacid,3-(4-nitrophenyl)-,1,1-dimethylethylester
- Purity
- 97%
- Packaging
- 100mg
- Price
- $104
- Updated
- 2021/12/16
- Product number
- CD11373483
- Product name
- tert-Butyl3-(4-nitrophenyl)azetidine-1-carboxylate
- Purity
- 97%
- Packaging
- 100mg
- Price
- $109
- Updated
- 2021/12/16
- Product number
- CD11373483
- Product name
- tert-Butyl3-(4-nitrophenyl)azetidine-1-carboxylate
- Purity
- 97%
- Packaging
- 250mg
- Price
- $197
- Updated
- 2021/12/16
tert-Butyl 3-(4-nitrophenyl)azetidine-1-carboxylate Chemical Properties,Usage,Production
Synthesis
636-98-6
254454-54-1
883901-62-0
(a) Synthesis of tert-butyl 3-(4-nitrophenyl)azetidine-1-carboxylate (16): 1,2-dibromoethane (0.146 mL, 1.69 mmol) was added to a vigorously stirred suspension of zinc powder (0.901 g, 13.8 mmol) in THF (3.5 mL) under nitrogen protection. The resulting suspension was heated at 80°F for 10 minutes. Subsequently, a solution of trimethylmethylsilyl chloride (0.202 mL, 1.59 mmol) in THF (1.75 mL) was added at room temperature and stirred for 4 minutes followed by the slow dropwise addition of tert-butyl 3-iodoazetidine-1-carboxylate (3.00 g, 10.6 mmol) in THF (3.5 mL), the dropwise addition process lasting 15 minutes. The reaction mixture was stirred at room temperature for 2 h, after which Pd2(dba)3 (0.155 g, 0.170 mmol) and tri-2-furanylphosphine (0.143 g, 0.615 mmol) were added, followed by a THF (18 mL) solution of 1-iodo-4-nitrobenzene (2.90 g, 11.7 mmol). The reaction mixture was heated at 55°C for 3 h. Upon completion of the reaction, the reaction was quenched with saturated aqueous sodium chloride solution (15 mL). The aqueous phase was extracted with dichloromethane (2 x 15 mL), the organic phases were combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CombiFlash Rf, 40 g SiO2 column, cyclohexane solution with 10-40% EtOAc) to afford the title compound 16 as a pale yellow oil (2.14 g, 72%).1H NMR (300 MHz, CDCl3) δ 8.24 (dd, J = 6.8, 1.9 Hz, 2H) 7.51 (d, J = 8.6 Hz, 2H), 4.41 (t, J = 8.7 Hz, 2H), 3.98 (dd, J = 8.5, 5.7 Hz, 2H), 3.89-3.81 (m, 1H), 1.49 (s, 9H).
References
[1] Patent: WO2014/26243, 2014, A1. Location in patent: Page/Page column 88
[2] Patent: WO2014/26242, 2014, A1. Location in patent: Page/Page column 133; 134
tert-Butyl 3-(4-nitrophenyl)azetidine-1-carboxylate Preparation Products And Raw materials
Raw materials
Preparation Products
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