Tert-butyl3-acetylpyrrolidine-1-carboxylate
- Product Name
- Tert-butyl3-acetylpyrrolidine-1-carboxylate
- CAS No.
- 858643-95-5
- Chemical Name
- Tert-butyl3-acetylpyrrolidine-1-carboxylate
- Synonyms
- N-Boc-3-acetyl-pyrrolidine;3-Acetyl-1-Boc-pyrrolidine;1-Boc-3-acetyl-pyrrolidine;Tert-butyl3-acetylpyrrolidine-1-carboxylate;3-Acetyl-pyrrolidine-1-carboxylic acid tert-butyl ester;1-Pyrrolidinecarboxylic acid, 3-acetyl-, 1,1-dimethylethyl e...;1-Pyrrolidinecarboxylic acid, 3-acetyl-, 1,1-dimethylethyl ester
- CBNumber
- CB12499210
- Molecular Formula
- C11H19NO3
- Formula Weight
- 213.27
- MOL File
- 858643-95-5.mol
Tert-butyl3-acetylpyrrolidine-1-carboxylate Property
- Boiling point:
- 293.8±33.0 °C(Predicted)
- Density
- 1.075±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- Chloroform, Ethyl Acetate
- form
- Oil
- pka
- -2.57±0.40(Predicted)
- color
- Clear Orangish Yellow
- optical activity
- -0.74°(C=1g/100ml MeOH)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H227Combustible liquid
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
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
- A170450
- Product name
- 3-Acetyl-1-Boc-pyrrolidine
- Packaging
- 100mg
- Price
- $140
- Updated
- 2021/12/16
- Product number
- V8137
- Product name
- tert-Butyl3-acetylpyrrolidine-1-carboxylate
- Packaging
- 100mg
- Price
- $131.6
- Updated
- 2021/12/16
- Product number
- CHM0096954
- Product name
- TERT-BUTYL-3-ACETYLPYRROLIDINE-1-CARBOXYLATE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $501.88
- Updated
- 2021/12/16
- Product number
- 122155
- Product name
- 1-Boc-3-acetyl-pyrrolidine
- Purity
- 97.0%
- Packaging
- 1g
- Price
- $1304
- Updated
- 2021/12/16
- Product number
- 75R0353
- Product name
- 1-Boc-3-acetyl-pyrrolidine
- Purity
- 98%
- Packaging
- 25g
- Price
- $1500
- Updated
- 2021/12/16
Tert-butyl3-acetylpyrrolidine-1-carboxylate Chemical Properties,Usage,Production
Uses
3-Acetyl-1-Boc-pyrrolidine is a boc protected reagent that is used for selective inhibitors of H. influenzae TrmD that mimic tRNA interaction by inducing TrmD lid domain ordering.
Synthesis
569667-93-2
75-16-1
858643-95-5
The general procedure for the synthesis of N-Boc-3-acetylpyrrolidine from tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate and methylmagnesium bromide was as follows: tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (4.0 g, 15.50 mmol) was dissolved in THF (70 ml) at 0 °C and under nitrogen protection and stirred. . 3M methylmagnesium bromide ether solution (26 ml, 78 mmol) was added slowly dropwise, keeping the reaction temperature at 0 °C. After the dropwise addition, the reaction mixture was continued to be stirred at 0°C for 30 minutes. Subsequently, the reaction mixture was slowly poured into saturated ammonium chloride solution (1 L) to quench the reaction and extracted with ethyl acetate (2 x 200 ml). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product tert-butyl 3-acetylpyrrolidine-1-carboxylate (3.0 g, 14.08 mmol), which was used directly in the subsequent reaction without further purification. The product was analyzed by LCMS (Method A) with a retention time of 3.83 min, and the mass spectrum (ES+) showed m/z of 157.89 (M-56).1H NMR (400 MHz, DMSO-d6) δ ppm: 3.77-3.40 (m, 2H), 3.22-3.25 (m, 3H), 2.17 (s, 3H), 2.03- 2.11 (m, 1H), 1.85-1.94 (m, 1H), 1.39 (s, 9H).
References
[1] Journal of Organic Chemistry, 2009, vol. 74, # 5, p. 1932 - 1938
[2] Patent: WO2010/51245, 2010, A1. Location in patent: Page/Page column 53
[3] Patent: US2010/298334, 2010, A1. Location in patent: Page/Page column 71-72
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 18, p. 7278 - 7288
[5] Patent: WO2017/103614, 2017, A1. Location in patent: Page/Page column 76; 78
Tert-butyl3-acetylpyrrolidine-1-carboxylate Preparation Products And Raw materials
Raw materials
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