Diisopropylethylamine → 2-{(3R)-1-[(3-pyridin-2-ylisoxazol-4-yl)carbonyl]piperidin-3-yl}propan-2-ol

HRID 1446284Notes

Reaction equation

HRID 1446284 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]([OH:11])([CH3:10])[CH3:9])[CH2:3]1.CN([C:15]([O:19][N:20]1N=[N:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.N1C=CC=C[C:44]=1[C:49]1[O:53]N=CC=1C(O)=O>CN(C=O)C>[N:27]1[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=1[C:21]1[C:44]([C:49]([N:2]2[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]([OH:11])([CH3:10])[CH3:9])[CH2:3]2)=[O:53])=[CH:15][O:19][N:20]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 223090705-(Pyridin-2-yl)-1,2-oxazole-4-carboxylic acidHCID 68537144(R)-2-(piperidin-3-yl)propan-2-ol hydrochloride

Product 1

HCID 686850212-{(3R)-1-[(3-pyridin-2-ylisoxazol-4-yl)carbonyl]piperidin-3-yl}propan-2-olYield 48.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[(3R)-piperidin-3-yl]propan-2-ol hydrochloride (7 mg, 0.039 mmol), TBTU (15 mg, 0.047 mmol, 1.2 equ.) and N-ethyl-N-isopropylpropan-2-amine (14 μL, 0.079 mmol, 2 equ.) in DMF (0.3 mL) was added to 5-pyridin-2-ylisoxazole-4-carboxylic acid (7 mg, 0.039 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 (6 mg). MS (ESI, pos. ion) m/z calcd for C17H21N3O3: 315.1583, found 315.1586.

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-6515d54e4e12421e856c87cbb832b7f9
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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