Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1446286Generated: October 25, 2026

Diisopropylethylamine → ((4R)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}-4-phenylpyrrolidin-3-yl)methanol

https://huagongshe.com/reaction/1446286

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
ReactantO-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733207—
Reactant(4-Phenylpyrrolidin-3-yl)methanolHCID 13316928—
Reactant5-(p-Tolyl)isoxazole-4-carboxylic acidHCID 22831706—
SolventDimethylformamideHCID 6228—
Product((4R)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}-4-phenylpyrrolidin-3-yl)methanolHCID 6868440933.4%

Reaction Steps

A solution of (4-phenylpyrrolidin-3-yl)methanol (7 mg, 0.033 mmol), TBTU (13 mg, 0.039 mmol, 1.2 equ.) and N-ethyl-N-isopropylpropan-2-amine (11 μL, 0.066 mmol, 2 equ.) in DMF (0.3 mL) was added to 5-(4-methylphenyl)isoxazole-4-carboxylic acid (7 mg, 0.033 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 (4 mg). MS (ESI, pos. ion) m/z calcd for C22H22N2O3: 362.1630, found 362.1629.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07666888B2
Source datasetuspto-grants-2010_02
ORD IDord-de973918f5334992b12fc13abd8e2201
Source noteuspto-grants-2010_02