Diisopropylethylamine → 3-(4-Fluorophenyl)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-ol

HRID 1446266Notes

Reaction equation

HRID 1446266 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]([OH:15])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.Cl.[F:48][C:49]1[CH:54]=[CH:53][C:52]([C:55]2([OH:60])[CH2:59][CH2:58][NH:57][CH2:56]2)=[CH:51][CH:50]=1>CN(C=O)C>[F:48][C:49]1[CH:50]=[CH:51][C:52]([C:55]2([OH:60])[CH2:59][CH2:58][N:57]([C:13]([C:9]3[CH:10]=[N:11][O:12][C:8]=3[C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[O:15])[CH2:56]2)=[CH:53][CH:54]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2005563-(4-Fluorophenyl)pyrrolidin-3-ol hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 228317065-(p-Tolyl)isoxazole-4-carboxylic acid

Product 1

HCID 591701583-(4-Fluorophenyl)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-olYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(4-methylphenyl)isoxazole-4-carboxylic acid (20 mg, 0.1 mmol), TBTU (39 mg, 0.12 mmol, 1,2 equ.) and N-ethyl-N-isopropylpropan-2-amine (35 μL, 0.2 mmol, 2 equ) in DMF (1 mL) was added to 3-(4-fluorophenyl)pyrrolidin-3-ol hydrochloride (22 mg, 0.1 mmol) and the reaction mixture was left 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 (30 mg). MS (ESI, pos. ion) m/z calcd for C21H19FN2O3: 366.1380, found 366.1380.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by RP-HPLC
  3. customAfter evaporation of the solvents the product
  4. customwas dried in vacuum

Sources & evidence

ORD record
ord-ca680add4033459f9bd46f1d710f1c70
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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