| Identification | Back Directory | [Name]
(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester | [CAS]
1428243-26-8 | [Synonyms]
intermediate of abt594
Upadacitinib intermediate
Upadacitinib intermediate5
(3R,4S)-3-(2-Bromoacetyl)-4-ethylpyrrolidine-1-carboxylate
(3R,4S)-benzyl 3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate
Benzyl (3R,4S)-3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate
(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
1-Pyrrolidinecarboxylic acid, 3-(2-bromoacetyl)-4-ethyl-, phenylmethyl ester, (3R,4S)- | [Molecular Formula]
C16H20BrNO3 | [MDL Number]
MFCD30802183 | [MOL File]
1428243-26-8.mol | [Molecular Weight]
354.24 |
| Chemical Properties | Back Directory | [Boiling point ]
453.1±45.0 °C(Predicted) | [density ]
1.361±0.06 g/cm3(Predicted) | [storage temp. ]
Storage temp. 2-8°C | [pka]
-2.91±0.60(Predicted) | [Appearance]
White to off-white Solid | [Optical Rotation]
25.6747°(C=1.0523g/100ml MEOH) | [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 |
| Hazard Information | Back Directory | [Uses]
(3R,4S)-3-(2-Bromoacetyl)-4-ethylpyrrolidine-1-carboxylate 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%). |
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