Diisopropylethylamine → 2-((3R)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}piperidin-3-yl)propan-2-ol

HRID 1446283Notes

Reaction equation

HRID 1446283 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(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:43][C:44]1[CH:49]=[CH:48][C:47]([C:50]2[O:54][N:53]=[CH:52][C:51]=2[C:55](O)=[O:56])=[CH:46][CH:45]=1>CN(C=O)C>[CH3:43][C:44]1[CH:45]=[CH:46][C:47]([C:50]2[O:54][N:53]=[CH:52][C:51]=2[C:55]([N:2]2[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]([OH:11])([CH3:10])[CH3:9])[CH2:3]2)=[O:56])=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 228317065-(p-Tolyl)isoxazole-4-carboxylic acidHCID 68537144(R)-2-(piperidin-3-yl)propan-2-ol hydrochloride

Product 1

HCID 591701572-((3R)-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}piperidin-3-yl)propan-2-olYield 70.3%

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-(4-methylphenyl)isoxazole-4-carboxylic acid (8 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 the product was dried in vacuum to yield the title compound (9 mg). MS (ESI, pos. ion) m/z calcd for C19H24N2O3: 328.1787, found 328.1784.

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-e6ad90f6e96a4a8ebe32cbdcaa187049
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

Loading…