Triacetoxyperiodinane → HCID 86670633, compound

HRID 1626319Notes

Reaction equation

HRID 1626319 reaction equation
[C:1]1([C:7]2[N:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:9]3[C:14]([N:15]=2)=[C:13]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])[N:12]=[CH:11][N:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]1([C:7]2[N:8]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:9]3[C:14]([N:15]=2)=[C:13]([NH:16][CH2:17][CH2:18][CH:19]=[O:20])[N:12]=[CH:11][N:10]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67205485HCID 67205485, compound

Product 1

HCID 86670633HCID 86670633, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 3-(8,9-diphenyl-9H-purin-6-ylamino)propan-1-ol obtained in step 1 (0.77 g, 2.24 mmol) in dichloromethane was added Dess-Martin (1.4 g, 3.37 mmol) at room temperature and stirred for 2 hours at room temperature. The resulting reaction mixture was concentrated under reduced pressure. The residue was diluted with CH2Cl2, and washed with water. The organic layer thus separated was dried over anhydrous MgSO4 and evaporated in vacuo to provide title compound (0.73 g, 94%) as yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. additionThe residue was diluted with CH2Cl2
  4. washwashed with water
  5. customThe organic layer thus separated
  6. dry with materialwas dried over anhydrous MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f5905b296ab24f15a590b6e41fdafdc0
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Reaction notes

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