Triacetoxyperiodinane → HCID 89601813, compound

HRID 526304Notes

Reaction equation

HRID 526304 reaction equation
[OH:1][CH:2]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]2[CH2:22][N:23]([CH3:26])[CH2:24][CH2:25][C:14]=12)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:26][N:23]1[CH2:24][CH2:25][C:14]2=[C:13]([C:2]([C:3]3[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=3)=[O:1])[C:21]3[C:16]([N:15]2[CH2:22]1)=[CH:17][CH:18]=[CH:19][CH:20]=3

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 89601758HCID 89601758, compound

Product 1

HCID 89601813HCID 89601813, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(hydroxy(2-methyl-1,2,3,4-tetrahydropyrimido[1,6-a]indol-5-yl)methyl)benzoate (400 mg) in 60 mL of CH2Cl2 was added 0.5 g of Dess-Martin reagent. After stirring for 10 min at r.t., the reaction was quenched with 25 mL of saturated aqueous solution of NaHCO3 and the CH2Cl2 phase was dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluted with up to 10% MeOH/EtOAc to give 80 mg of the title product as white solid.

Workup

  1. customthe reaction was quenched with 25 mL of saturated aqueous solution of NaHCO3
  2. dry with materialthe CH2Cl2 phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with up to 10% MeOH/EtOAc

Sources & evidence

ORD record
ord-fb1d6da2a20e45ecaaef21d1f92a1d65
Source dataset
uspto-grants-2016_05
Patent number
US09345905B2

Reaction notes

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