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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1446289Generated: October 26, 2026

Diisopropylethylamine → 3-(2-Chlorophenyl)-1-{[3-(4-methylphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-ol

https://huagongshe.com/reaction/1446289

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantO-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733207—
Reactant3-Pyrrolidinol, 3-(o-chlorophenyl)-, hydrochlorideHCID 3051543—
Reactant3-(4-Methylphenyl)isoxazole-4-carboxylic acidHCID 58828797—
SolventDimethylformamideHCID 6228—
Product3-(2-Chlorophenyl)-1-{[3-(4-methylphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-olHCID 5917019773.7%

Reaction Steps

A solution of 3-(2-chlorophenyl)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 (11 mg). MS (ESI, pos. ion) m/z calcd for C21H19ClN2O3: 382.1084, found 382.1080.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07666888B2
Source datasetuspto-grants-2010_02
ORD IDord-463eafc9f03249a58881c11a50100ee7
Source noteuspto-grants-2010_02