Diisopropylethylamine → 1-{[5-(4-Fluorophenyl)isoxazol-4-yl]carbonyl}-5-methyl-3-phenylpyrrolidin-3-ol

HRID 1446342Notes

Reaction equation

HRID 1446342 reaction equation
C(N(C(C)C)C(C)C)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:21][N:20]=[CH:19][C:18]=2[C:22]([OH:24])=O)=[CH:13][CH:12]=1.[CH3:25][CH:26]1[NH:30][CH2:29][C:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([OH:31])[CH2:27]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[O:21][N:20]=[CH:19][C:18]=2[C:22]([N:30]2[CH:26]([CH3:25])[CH2:27][C:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([OH:31])[CH2:29]2)=[O:24])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 30513955-Methyl-3-phenyl-pyrrolidin-3-olHCID 37233755-(4-Fluorophenyl)isoxazole-4-carboxylic acid

Product 1

HCID 591701871-{[5-(4-Fluorophenyl)isoxazol-4-yl]carbonyl}-5-methyl-3-phenylpyrrolidin-3-olYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-ethyl-N-isopropylpropan-2-amine (14 μL, 0.04 mmol) was added to a solution of 5-(4-fluorophenyl)isoxazole-4-carboxylic acid (8 mg, 0.04 mmol), 5-methyl-3-phenylpyrrolidin-3-ol (7 mg, 0.04 mmol) and TBTU (15 mg, 0.048 mmol, 1.2 equ.) in DMF (0.3 mL) at rt. The reaction mixture was left at rt for 2 h. The crude product was purified by RP-HPLC. After evaporation of the solvents the product was dried in vacuum to yield the title compound (11 mg). MS (ESI, pos. ion) m/z: calcd for C21H19FN2O3: 366.1380, found 366.1391.

Workup

  1. customThe crude product was purified by RP-HPLC
  2. customAfter evaporation of the solvents the product
  3. customwas dried in vacuum

Sources & evidence

ORD record
ord-ed704f59dab74532b17c695f4378ca94
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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