Diisopropylethylamine → {(4R)-4-phenyl-1-[(5-pyridin-2-ylisoxazol-4-yl)carbonyl]pyrrolidin-3-yl}methanol

HRID 1446287Notes

Reaction equation

HRID 1446287 reaction equation
[C:1]1([CH:7]2[CH2:11][NH:10][CH2:9][CH:8]2[CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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.[N:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[C:51]1[O:55][N:54]=[CH:53][C:52]=1[C:56](O)=[O:57]>CN(C=O)C>[C:1]1([C@@H:7]2[CH2:11][N:10]([C:56]([C:52]3[CH:53]=[N:54][O:55][C:51]=3[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][N:45]=3)=[O:57])[CH2:9][CH:8]2[CH2:12][OH:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 13316928(4-Phenylpyrrolidin-3-yl)methanolHCID 223090705-(Pyridin-2-yl)-1,2-oxazole-4-carboxylic acid

Product 1

HCID 68683047{(4R)-4-phenyl-1-[(5-pyridin-2-ylisoxazol-4-yl)carbonyl]pyrrolidin-3-yl}methanolYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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-pyridin-2-ylisoxazole-4-carboxylic acid (6 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 from the pure fractions, the residue was dissolved in chloroform and washed with diluted NaOH to provide the neutral compound in the organic phase that was dried (Na2SO4) and evaporated and dried in vacuum to yield the title compound (3 mg). MS (ESI, pos. ion) m/z calcd for C20H19N3O3: 349.1426, found 349.1427.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by RP-HPLC
  3. customAfter evaporation of the solvents from the pure fractions
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with diluted NaOH
  6. customto provide the neutral compound in the organic phase that
  7. dry with materialwas dried (Na2SO4)
  8. customevaporated
  9. customdried in vacuum

Sources & evidence

ORD record
ord-455bdb12276c450c81f770d057345e5c
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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