Triacetoxyperiodinane → HCID 23077588, compound

HRID 1349462Notes

Reaction equation

HRID 1349462 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:31])[CH:11]=[C:12]([CH2:29][OH:30])[N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[C:15](=[O:28])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10](=[O:31])[CH:11]=[C:12]([CH:29]=[O:30])[N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[C:15](=[O:28])[C:14]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 23077651HCID 23077651, compound

Product 1

HCID 23077588HCID 23077588, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 9-benzyloxy-2-(3,4-dichlorobenzyl)-6-hydroxymethyl-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (860 mg) obtained in Example 5, Step 6 in chloroform (80 ml) was added Dess-Martin reagent (843 mg). After stirring at room temperature for 1 hr, the solvent was evaporated and chloroform (50 ml) was added to the obtained residue and a solid product was filtered off. The filtrate was concentrated and purified by silica gel column chromatography (chloroform:acetone=1:2) to give 9-benzyloxy-2-(3,4-dichlorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazine-6-carbaldehyde (621 mg).

Workup

  1. customthe solvent was evaporated
  2. additionchloroform (50 ml) was added to the obtained residue
  3. filtrationa solid product was filtered off
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography (chloroform:acetone=1:2)

Sources & evidence

ORD record
ord-1bcc68c524f6414c9434af94b5a31b15
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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