Tetrabutylammonium Fluoride → HCID 44230672, compound

HRID 1665433Notes

Reaction equation

HRID 1665433 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21](=[O:54])[CH2:22][CH2:23][CH2:24][C:25]#[C:26][CH2:27][C@@H:28]1[C@@H:32]([CH2:33][O:34][Si](C(C)(C)C)(C)C)[CH2:31][N:30]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][C:44]=2[O:51][CH3:52])[C:29]1=[O:53]>C1COCC1>[CH3:19][O:20][C:21](=[O:54])[CH2:22][CH2:23][CH2:24][C:25]#[C:26][CH2:27][C@@H:28]1[C@@H:32]([CH2:33][OH:34])[CH2:31][N:30]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][C:44]=2[O:51][CH3:52])[C:29]1=[O:53]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68579426HCID 68579426, compound

Product 1

HCID 44230672HCID 44230672, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1.0 M in THF, 4.0 mL, 4.0 mmol) was added to a solution of 7-[(3R*,4R*)-4-(tert-butyldimethylsilanyloxymethyl)-1-(2,4-dimethoxybenzyl)-2-oxo-pyrrolidin-3-yl]-hept-5-ynoic acid methyl ester (680 mg, 1.31 mmol) in THF (13 mL) at 0° C. under nitrogen. The reaction was allowed to warm to room temperature. After 18 h at room temperature, THF was removed in vacuo and the residue was taken up in EtOAc (50 mL). The organic phase was washed with water (2×20 mL) and brine (20 mL) then dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography on silica gel (85% EtOAc/hexane→EtOAc, gradient) to afford 304 mg (57%) of 7-[(3R*,4R*)-1-(2,4-dimethoxybenzyl)-4-hydroxymethyl-2-oxo-pyrrolidin-3-yl]-hept-5-ynoic acid methyl ester.

Workup

  1. customTHF was removed in vacuo
  2. washThe organic phase was washed with water (2×20 mL) and brine (20 mL)
  3. dry with materialthen dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash column chromatography on silica gel (85% EtOAc/hexane→EtOAc, gradient)

Sources & evidence

ORD record
ord-ae2135e2d377405497a4d3c494e4670a
Source dataset
uspto-grants-2011_10
Patent number
US08039507B2

Reaction notes

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