2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester
- Product Name
- 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester
- CAS No.
- 149682-75-7
- Chemical Name
- 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester
- Synonyms
- 1-(Tert-butoxycarbonyl)pyrrolidin-2-ylboronic acid;1-N-BOC-pyrrolidin-2-boronicacid;1-N-Boc-Pyrrolidin-2-ylboronicaci;N-Boc-pyrrolidin-2-yl]boronic Acid;Aditoprim Impurity 2 Hydrochloride;1-N-Boc-pyrrolidin-2-ylboronic acid;1-N-Boc-pyrrolidin-2-ylboronic acid, 95+%;1-(tert-butoxycarbonyl)pyrrolidin-2-yl-2-boronic;1-(tert-butoxycarbonyl)pyrrolidin-2-yl-2-boronic acid;(+/-)-1-(T-Butoxycarbonyl)-Pyrrolidine-2-Boronic Acid
- CBNumber
- CB01074079
- Molecular Formula
- C9H18BNO4
- Formula Weight
- 215.05
- MOL File
- 149682-75-7.mol
2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester Property
- Boiling point:
- 349.2±52.0 °C(Predicted)
- Density
- 1.15±0.1 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Store in freezer, under -20°C
- solubility
- Chloroform (Slightly, Heated), DMSO (Slightly)
- pka
- 9.94±0.20(Predicted)
- form
- Solid
- color
- Yellow
Safety
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- 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
- B665855
- Product name
- N-Boc-pyrrolidin-2-ylboronicAcid
- Packaging
- 250mg
- Price
- $90
- Updated
- 2021/12/16
- Product number
- B547
- Product name
- 1-Boc-Pyrrolidine-2-boronicacid
- Packaging
- 5g
- Price
- $94
- Updated
- 2021/12/16
- Product number
- 074037
- Product name
- 1-N-Boc-pyrrolidin-2-ylboronic acid
- Purity
- 95+%
- Packaging
- 5g
- Price
- $110
- Updated
- 2021/12/16
- Product number
- FB38548
- Product name
- 1-Boc-Pyrrolidine-2-boronic acid
- Packaging
- 2g
- Price
- $120
- Updated
- 2021/12/16
- Product number
- B547
- Product name
- 1-Boc-Pyrrolidine-2-boronicacid
- Packaging
- 1g
- Price
- $29
- Updated
- 2021/12/16
2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester Chemical Properties,Usage,Production
Chemical Properties
White Solid
Uses
2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester is used as a boc-protected cyclic amine so as to used in the preparation of heterocyclic boronic acid compounds.
Synthesis
121-43-7
149682-75-7
N-Boc-pyrrolidine (20 g, 117 mmol, 1 eq.) and anhydrous THF (60 mL) were added to a pre-flame-dried round-bottomed flask equipped with a magnetic stirrer under nitrogen protection. The resulting clarified colorless solution was cooled to -78 °C, followed by the slow addition of s-BuLi solution (100 mL of 1.4 M cyclohexane solution, 140 mmol) over 30 min. The light orange solution was kept stirred at -78 °C for 3 h. B(OMe)3 (39 mL, 350 mmol) was then added. The cooling bath was removed and the clear colorless solution was allowed to warm slowly to 0 °C. Upon reaching 0 °C, the reaction was quenched with a small amount of water (~2 mL) and allowed to gradually warm to room temperature, followed by extraction with 2N NaOH (250 mL) and backwashing with EtOAc (150 mL). The aqueous phase was acidified to pH 3 with 2N HCl and extracted with EtOAc (3 x 120 mL). The organic phases were combined, dried over Na2SO4, and concentrated to give free boric acid (22.08 g, 103 mmol) as a viscous white solid in 88% yield. Without further purification, boric acid was dissolved in tert-butyl methyl ether (150 mL) and (+)-pyridinediol (17.5 g, 103 mmol) was added with continuous stirring at room temperature. after 18 h, the ether was removed by evaporation, and (+)-diethanolboronate was purified by column chromatography (silica gel, 1:3 hexanes/EtOAc) to give a clarified thick oily substance (26.84 g 76.8 mmol, 76% yield, Rf=0.6, observed by 12 and/or PMA staining using a 2:1 hexane/ethyl acetate eluent). The oil was dissolved in anhydrous ether, cooled to 0 °C in an ice bath and passed through dry HCl gas with continuous stirring for 10 min to remove the Boc protecting groups.After 2 h, a white precipitate was formed in the flask, and the ether and excess HCl were removed in vacuo to give the racemic HCl salt as a white solid. The HCl salt was dissolved in a minimal amount of dichloromethane (250 mL), gently heated to promote dissolution, followed by continuous stirring for 8 h to form a fluffy white precipitate (collected by vacuum filtration). After filtration and drying, the precipitate was dissolved in a very small amount of 2-propanol (about 200 mL) and gently heated until homogeneous. The alcohol solution was stirred overnight and the resulting white precipitate was collected by vacuum filtration to give isomerically pure 1 as a white solid (7.0 g, 27 mmol, 23% yield).1H NMR (400 MHz, D2O) δ 4.28 (d, J=8.0 Hz, 1H), 3.06 (m, 3H), 2.18 (m, 1H), 1.96 (m, 2H), 1.96 (m, 2H) 1.78 (m, 3H), 1.62 (m, 2H), 1.21 (s, 3H), 1.05 (m, 5H), 0.84 (d, J=12Hz, 2H), 0.71 (s, 2H), 0.62 (s, 3H).
References
[1] Patent: WO2005/47297, 2005, A1. Location in patent: Page/Page column 114-115
[2] Patent: US2006/276435, 2006, A1. Location in patent: Page/Page column 25
2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester manufacturers
- Product
- 1-N-boc-pyrrolidin-2-ylboronic acid 149682-75-7
- Price
- US $3.00-9.00/KG
- Min. Order
- 0.1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2025-07-05
- Product
- 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester 149682-75-7
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-09-27
- Product
- 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester 149682-75-7
- Price
- US $1.00/g
- Min. Order
- 1g
- Purity
- 99.99%
- Supply Ability
- 200kg
- Release date
- 2019-12-20