Diisopropylethylamine → 1-[(5-Benzylisoxazol-4-yl)carbonyl]-3-phenylpyrrolidin-3-ol

HRID 1446276Notes

Reaction equation

HRID 1446276 reaction equation
[CH2:1]([C:8]1[O:12][N:11]=[CH:10][C:9]=1[C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[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.[C:48]1([C:54]2([OH:59])[CH2:58][CH2:57][NH:56][CH2:55]2)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C>[CH2:1]([C:8]1[O:12][N:11]=[CH:10][C:9]=1[C:13]([N:56]1[CH2:57][CH2:58][C:54]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)([OH:59])[CH2:55]1)=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2002803-Phenylpyrrolidin-3-ol hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 147872525-Benzyl-4-isoxazolecarboxylic acid

Product 1

HCID 591701181-[(5-Benzylisoxazol-4-yl)carbonyl]-3-phenylpyrrolidin-3-olYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-benzylisoxazole-4-carboxylic acid (10 mg, 0.05 mmol), TBTU (19 mg, 0.06 mmol, 1,2 equ.) and N-ethyl-N-isopropylpropan-2-amine (17 μL, 0.10 mmol, 2 equ) in DMF (0.3 mL) was added to 3-phenylpyrrolidin-3-ol hydrochloride (10 mg, 0.05 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 (4 mg). MS (ESI, pos. ion) m/z calcd for C21H20N2O3: 348.1474, found 348.1481.

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-500eb554a7344b95aba94592e2179daf
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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