Triacetoxyperiodinane → HCID 86691983, compound

HRID 931827Notes

Reaction equation

HRID 931827 reaction equation
[Br:1][C:2]1[C:11]([C@H:12]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:23])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:24][OH:25])=[N:7]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Br:1][C:2]1[C:11]([C@H:12]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:23])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH:24]=[O:25])=[N:7]2

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68585446HCID 68585446, compound

Product 1

HCID 86691983HCID 86691983, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-ethyl 2-(5-bromo-2-(hydroxymethyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetate (200 mg, 0.49 mmol) in anhydrous dichloromethane (13 mL) at 0° C. was added Dess-Martin periodinane (248 mg, 0.58 mmol) and the reaction mixture was stirred for 1 hour. Reaction mixture was partitioned between dichloromethane and water and organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a white solid (160 mg, 80%). LCMS-ESI+ (m/z): [M+H]+ calcd for C19H23BrNO4: 408.07. found: 408.88, 410.14

Workup

  1. customReaction mixture
  2. customwas partitioned between dichloromethane and water and organic layer
  3. concentrationwas concentrated
  4. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ef03bb7bf21740bcaafcfcfedb9cd42a
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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