(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester Chemical Properties

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 Usage And Synthesis

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(1428243-26-8)Related Product Information

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