Tetrabutylammonium Fluoride → HCID 59614360, compound

HRID 409471Notes

Reaction equation

HRID 409471 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH3:14])[CH2:11][C@H:10]([O:15][Si](C(C)(C)C)(C)C)[C@@H:9]1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH3:14])[CH2:11][C@H:10]([OH:15])[C@@H:9]1[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59614342HCID 59614342, compound

Product 1

HCID 59614360HCID 59614360, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S,3S,5R)-2-benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.243 mmol; 102 mg) in THF is added 1.0 M THF solution (0.36 mL) of tetra-n-butylammonium fluoride under nitrogen at room temperature. After 3 hours, The reaction mixture is quenched with saturated aqueous ammonium chloride solution, extracted three times with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc) to give (2S,3S,5R)-2-benzyl-5-ethyl-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (74.4 mg, 99%); ESI-MS m/z: 250 [M+−tBu+2], Retention time 2.34 min (condition A).

Workup

  1. customThe reaction mixture is quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc)

Sources & evidence

ORD record
ord-c363b3fc180f41ceabbb3bd75639f8f2
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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