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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1446288Generated: October 26, 2026

Diisopropylethylamine → 3-(4-Fluoro-3-methylphenyl)-1-{[3-(4-methylphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-ol

https://huagongshe.com/reaction/1446288

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantO-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733207—
Reactant3-(4-Methylphenyl)isoxazole-4-carboxylic acidHCID 58828797—
Reactant3-(4-Fluoro-3-methylphenyl)pyrrolidin-3-ol hydrochlorideHCID 68685567—
SolventDimethylformamideHCID 6228—
Product3-(4-Fluoro-3-methylphenyl)-1-{[3-(4-methylphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-olHCID 5917024680.9%

Reaction Steps

A solution of 3-(4-fluoro-3-methylphenyl)pyrrolidin-3-ol hydrochloride (9 mg, 0.039 mmol), TBTU (15 mg, 0.047 mmol, 1.2 equ.) and N-ethyl-N-isopropylpropan-2-amine (14 μL, 0.079 mmol, 2 equ.) in DMF (0.3 mL) was added to 3-(4-methylphenyl)isoxazole-4-carboxylic acid (8 mg, 0.039 mmol) and the reaction mixture was stirred at rt for 2 h. The solvent was evaporated and the crude product was purified by RP-HPLC. After evaporation of the solvents the product was dried in vacuum to yield the title compound (12 mg). MS (ESI, pos. ion) m/z calcd for C22H21FN2O3: 380.1536, found 380.1532.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07666888B2
Source datasetuspto-grants-2010_02
ORD IDord-9220ebb7b4974d1b91cd6e6545be8cee
Source noteuspto-grants-2010_02