Triacetoxyperiodinane → HCID 86673117, compound

HRID 1853356Notes

Reaction equation

HRID 1853356 reaction equation
[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][OH:18])[CH:15]=2)[O:10][C:9]([C:19]2[N:24]=[CH:23][N:22]3[CH:25]=[CH:26][CH:27]=[C:21]3[CH:20]=2)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=2)[O:10][C:9]([C:19]2[N:24]=[CH:23][N:22]3[CH:25]=[CH:26][CH:27]=[C:21]3[CH:20]=2)=[CH:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 86673118HCID 86673118, compound

Product 1

HCID 86673117HCID 86673117, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-Hydroxymethyl-2-pyrrolo[1,2-c]pyrimidin-3-yl-chromen-4-one O-tert-butyl-oxime (example 144C) (575 mg, 1.58 mmol) in dichloromethane (60 ml), was added a Dess Martin solution (15 wt. % in DCM) (6.7 ml; 2.37 mmol). After 1 hour stirring at room temperature, an additional amount of Dess Martin solution (6 ml) was added to complete the reaction. The reaction mixture was quenched with water and added to a 1:1 solution of saturated sodium hydrogenocarbonate and 5% aq solution of Na2S2O3. After extraction with ethyl acetate, the organic layers were washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 0-40%) to afford the title compound (355 mg, 62%) as a yellow solid.

Workup

  1. customthe reaction
  2. customThe reaction mixture was quenched with water
  3. additionadded to a 1:1 solution of saturated sodium hydrogenocarbonate and 5% aq solution of Na2S2O3
  4. extractionAfter extraction with ethyl acetate
  5. washthe organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography over silica gel (gradient cyclohexane/ethyl acetate: 0-40%)

Sources & evidence

ORD record
ord-8e935d35d10240498b85ffb7e4588558
Source dataset
uspto-grants-2015_02
Patent number
US08962627B2

Reaction notes

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