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

HRID 1446350Notes

Reaction equation

HRID 1446350 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]([OH:16])=O)=[CH:12][O:11][N:10]=2)=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[Cl:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=1[C:56]1([OH:61])[CH2:60][CH2:59][NH:58][CH2:57]1>CN(C=O)C>[Cl:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=1[C:56]1([OH:61])[CH2:60][CH2:59][N:58]([C:14]([C:13]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[N:10][O:11][CH:12]=2)=[O:16])[CH2:57]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 30515433-Pyrrolidinol, 3-(o-chlorophenyl)-, hydrochlorideHCID 591701213-(4-Methoxyphenyl)isoxazole-4-carboxylic acid

Product 1

HCID 591701513-(2-Chlorophenyl)-1-{[3-(4-methoxyphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-olYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-methoxyphenyl)isoxazole-4-carboxylic acid (7 mg, 0.03 mmol), N-ethyl-N-isopropylpropan-2-amine (16 μL, 0.09 mmol, 3 equ.) and TBTU (12 mg, 0.036 mmol, 1.2 equ.) in DMF (0.3 mL) was added to 3-(2-chlorophenyl)pyrrolidin-3-ol hydrochloride (7 mg, 0.03 mmol). After 1 h at rt the crude product was purified by RP-HPLC. The pure fractions were basified (NaHCO3) and extracted with ethyl acetate, dried (Na2SO4), evaporated and dried in vacuum to yield the title compound (9 mg). MS (ESI, pos. ion) m/z: calcd for C21H19ClN2O4: 398.1033, found 398.1036.

Workup

  1. customAfter 1 h at rt the crude product was purified by RP-HPLC
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customdried in vacuum

Sources & evidence

ORD record
ord-f8054cdbabf746ddb05480a60bbbf5b9
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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