tert-butyl 3-Methylenepyrrolidine-1-carboxylate
- Product Name
- tert-butyl 3-Methylenepyrrolidine-1-carboxylate
- CAS No.
- 114214-71-0
- Chemical Name
- tert-butyl 3-Methylenepyrrolidine-1-carboxylate
- Synonyms
- N-Boc-3-methylenepyrrolidine;1-Boc-3-Methylenepyrrolid...;1-Boc-3-Methylene-pyrrolidine;tert-butyl 3-Methylenepyrrolidine-1-carboxylate;tert-butyl 3-methylidenepyrrolidine-1-carboxylate;3-Methylene-1-pyrrolidinecarboxylic acid tert-butyl ester;1-Pyrrolidinecarboxylic acid, 3-methylene-, 1,1-dimethylethy...;1-Pyrrolidinecarboxylic acid, 3-Methylene-, 1,1-diMethylethyl ester
- CBNumber
- CB82549697
- Molecular Formula
- C10H17NO2
- Formula Weight
- 183.25
- MOL File
- 114214-71-0.mol
tert-butyl 3-Methylenepyrrolidine-1-carboxylate Property
- Boiling point:
- 236.7±29.0 °C(Predicted)
- Density
- 1.01±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C
- pka
- -1.49±0.20(Predicted)
- Appearance
- Colorless to light yellow Liquid
Safety
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
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
- M304135
- Product name
- 3-Methylenepyrrolidine-1-carboxylicAcidtert-ButylEster
- Packaging
- 1g
- Price
- $160
- Updated
- 2021/12/16
- Product number
- 2362AA
- Product name
- tert-Butyl3-methylenepyrrolidine-1-carboxylate
- Packaging
- 250mg
- Price
- $96
- Updated
- 2021/12/16
- Product number
- OR914414
- Product name
- tert-Butyl3-methylidenepyrrolidine-1-carboxylate
- Purity
- 95%
- Packaging
- 1g
- Price
- $150
- Updated
- 2021/12/16
- Product number
- 4H56-1-PG
- Product name
- 1-Boc-3-methylenepyrrolidine
- Packaging
- 1g
- Price
- $185
- Updated
- 2021/12/16
- Product number
- OR914414
- Product name
- tert-Butyl3-methylidenepyrrolidine-1-carboxylate
- Purity
- 95%
- Packaging
- 5g
- Price
- $435
- Updated
- 2021/12/16
tert-butyl 3-Methylenepyrrolidine-1-carboxylate Chemical Properties,Usage,Production
Uses
3-Methylenepyrrolidine-1-carboxylic Acid tert-Butyl Ester, can be used as an intermediate for variety of chemical synthesis. It can be used for the preparation of aminomethylated 4-fluoropiperidines and 3-fluoropyrrolidines, which are of specific interest as bifunctional building blocks for fluorinated pharmaceutical compds.
Synthesis
1779-49-3
101385-93-7
114214-71-0
Step A: Synthesis of tert-butyl 3-methylene pyrrolidine-1-carboxylate. To a suspension consisting of methyltriphenylphosphonium bromide (18 g, 51 mmol) and tetrahydrofuran (THF, 200 mL) was slowly added n-butyllithium (1.6 M hexane solution, 32 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 5 min before a solution of 1-tert-butoxycarbonyl-3-pyrrolidone (9.0 g, 48 mmol) in THF (40 mL) was added via cannula. The reaction mixture was kept stirred at 0 °C for 90 min, followed by warming up to room temperature and continued stirring for 1 hour. Upon completion of the reaction, the mixture was cooled to 0 °C and quenched with saturated aqueous sodium bicarbonate (NaHCO3) and aqueous ammonium chloride (NH4Cl), followed by extraction with ether (Et2O). The organic layers were combined, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure. The crude product was suspended with hot hexane and filtered, and the filtrate was concentrated and purified by fast column chromatography (FCC) to afford the target compound tert-butyl 3-methylene pyrrolidine-1-carboxylate (4.4 g, 50% yield).
References
[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 21, p. 9738 - 9755
[2] Patent: WO2015/35278, 2015, A1. Location in patent: Page/Page column 81
[3] Patent: WO2010/141809, 2010, A1. Location in patent: Page/Page column 64
[4] Patent: US2014/45813, 2014, A1. Location in patent: Paragraph 0110; 0111
[5] Patent: US2014/275014, 2014, A1. Location in patent: Paragraph 0128; 0129; 0130
tert-butyl 3-Methylenepyrrolidine-1-carboxylate Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from tert-butyl 3-Methylenepyrrolidine-1-carboxylate manufacturers
- Product
- tert-butyl 3-Methylenepyrrolidine-1-carboxylate 114214-71-0
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20kg
- Release date
- 2018-08-07