Triacetoxyperiodinane → (S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid [3-(1,1-dimethyl-2-oxo-ethyl)-isoxazol-5-yl]amide

HRID 538649Notes

Reaction equation

HRID 538649 reaction equation
[OH:1][CH2:2][C:3]([C:6]1[CH:10]=[C:9]([NH:11][C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:13])[O:8][N:7]=1)([CH3:5])[CH3:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:5][C:3]([C:6]1[CH:10]=[C:9]([NH:11][C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[O:13])[O:8][N:7]=1)([CH3:4])[CH:2]=[O:1]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67457548(S)-1-(tetrahydro-pyran-4-yl)pyrrolidine-2-carboxylic acid [3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]amide

Product 1

HCID 117655527(S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid [3-(1,1-dimethyl-2-oxo-ethyl)-isoxazol-5-yl]amideYield 52.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To 180 mg (0.53 mmol) of (S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid [3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-amide in DCM (1.74 mL) are added 317 mg (0.75 mmol) of (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin-periodinane). The reaction mixture is stirred at RT for 1 h, diluted with sat. aq. NaHCO3 solution and stirred for additonal 30 min. The layers are separated; the organic layer is washed with brine and dried over Na2SO4. The solvent is removed under reduced pressure, the residue is purified by silica gel chromatographie (eluent: EE) to afford 93.0 mg of (S)-1-(tetrahydro-pyran-4-yl)-pyrrolidine-2-carboxylic acid [3-(1,1-dimethyl-2-oxo-ethyl)-isoxazol-5-yl]amide. Yield: 52%; ESI-MS: 336 [M+H]+; HPLC (Rt): 1.12 min (method E)

Workup

  1. stirringstirred for additonal 30 min
  2. customThe layers are separated
  3. washthe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by silica gel chromatographie (eluent: EE)

Sources & evidence

ORD record
ord-231a0b4df2844ed28c62f0b7046b78f9
Source dataset
uspto-grants-2014_10
Patent number
US08865744B1

Reaction notes

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