Diisopropylethylamine → HCID 56851159, compound

HRID 1690776Notes

Reaction equation

HRID 1690776 reaction equation
[F:1][C:2]([F:16])([F:15])[C@H:3]([CH3:14])[O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O.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.[O:48]1[CH2:53][CH2:52][CH:51]([C:54]2[CH:55]=[C:56]3[C:60](=[CH:61][CH:62]=2)[CH2:59][NH:58][CH2:57]3)[CH2:50][CH2:49]1>CN(C=O)C>[O:48]1[CH2:53][CH2:52][CH:51]([C:54]2[CH:55]=[C:56]3[C:60](=[CH:61][CH:62]=2)[CH2:59][N:58]([C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][C@@H:3]([CH3:14])[C:2]([F:1])([F:16])[F:15])=[O:9])[CH2:57]3)[CH2:50][CH2:49]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 56851158HCID 56851158, compoundHCID 577536035-(tetrahydro-pyran-4-yl)-2,3-dihydro-1H-isoindole

Product 1

HCID 56851159HCID 56851159, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.9 g (3.8 mmol) 2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid in 9 ml DMF under argon at room temperature, was added 1.4 g (4.2 mmol) TBTU, 3.3 ml (19.2 mmol) N-ethyldiisopropylamine and finally 0.8 g (3.8 mmol) 5-(tetrahydro-pyran-4-yl)-2,3-dihydro-1H-isoindole (CAS: 905274-50-2). The mixture was stirred at room temperature overnight. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate. The solution was washed twice with water and twice with sat. NaHCO3 solution, dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 1.5 g (93%) of the title compound as a yellow oil. MS (m/e): 420.2 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution was washed twice with water and twice with sat. NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
  8. customformed from heptane and ethylacetate

Sources & evidence

ORD record
ord-7acfb2c2330b4cd1b1c27073f97d6a2e
Source dataset
uspto-grants-2012_04
Patent number
US08153679B2

Reaction notes

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