(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
- CAS No.
- 1428243-26-8
- Chemical Name:
- (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
- Synonyms
- (3R,4S)-benzyl 3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate;Upadacitinib intermediate;1-Pyrrolidinecarboxylic acid, 3-(2-bromoacetyl)-4-ethyl-, phenylmethyl ester, (3R,4S)-;Benzyl (3R,4S)-3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate;Upatinib intermediate;intermediate of abt594;Upadacitinib Impurity 14;Upadacitinib intermediate5;Upadacitinib Intermediate1;1428243-26-8
- CBNumber:
- CB93311984
- Molecular Formula:
- C16H20BrNO3
- Molecular Weight:
- 354.24
- MOL File:
- 1428243-26-8.mol
- Modify Date:
- 2024/4/1 18:08:31
| Boiling point | 453.1±45.0 °C(Predicted) |
|---|---|
| Density | 1.361±0.06 g/cm3(Predicted) |
| pka | -2.91±0.60(Predicted) |
| InChI | InChI=1S/C16H20BrNO3/c1-2-13-9-18(10-14(13)15(19)8-17)16(20)21-11-12-6-4-3-5-7-12/h3-7,13-14H,2,8-11H2,1H3/t13-,14+/m1/s1 |
| InChIKey | QEFUCTKHMXMWRF-KGLIPLIRSA-N |
| SMILES | N1(C(OCC2=CC=CC=C2)=O)C[C@@H](CC)[C@@H](C(CBr)=O)C1 |
(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester Chemical Properties,Uses,Production
Uses
(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester is a reagent in the preparation of imidazopyrrolopyrazine derivatives and analogs for use as protein kinase modulators.
Preparation
Dimethylsulfoxonium 2-((3R,4S)-1-benzyloxycarbonyl-4-ethylpyrrolidin-3-yl)-2-oxo-ethylide (10.0 g, 28.5 mmol, 1.0 equivalents), THF (100 mL), and 33% HBr in AcOH (8.37 g, 34.1 mmol, 1.2 equivalents) were charged sequentially and heated to 40° C. The reaction mixture was agitated for 5 hours, cooled to 20° C, and then distilled under vacuum to approximately 65 mL. EtOAc (20 mL) and heptane (50 mL) were charged, and the reaction mixture was washed with water (5×50 mL). The organic layer was concentrated under vacuum and chased with EtOAc (2×50 mL) concentrating to dryness each time. N,N-dimethylacetamide (20 mL) was then charged to provide 30.8 g of a 24.0 wt/wt % solution of (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester (yield: 73%). 
(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
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| Zhejiang Brunova Technology Co., Ltd. | 8617857108485 17857108485 | China | 40 | 58 | Inquiry |
| Heading （Nanjing）Pharmtechnologies Co., Ltd. | +86-25-58467899-832 +86-13382406280 | China | 46 | 58 | Inquiry |
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| Shanghai Daken Advanced Materials Co.,Ltd | +86-371-66670886 | China | 16220 | 58 | Inquiry |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | China | 21676 | 55 | Inquiry |
| career henan chemical co | +86-0371-86658258 +8613203830695 | China | 29901 | 58 | Inquiry |
| SHANGHAI T&W PHARMACEUTICAL CO., LTD. | +86-021-61551413 +8618813727289 | China | 5738 | 58 | Inquiry |
| Neostar United (Changzhou) Industrial Co., Ltd. | +86-519-519-85557386 | China | 12210 | 58 | Inquiry |
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