Nitrogen → HCID 57556918, compound

HRID 503208Notes

Reaction equation

HRID 503208 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][CH2:9][C:10]1[CH:11]=[C:12]([N:16]2[C:20]3[CH:21]=[CH:22][C:23]([CH2:25][OH:26])=[CH:24][C:19]=3[N:18]=[CH:17]2)[CH:13]=[CH:14][CH:15]=1.N#N.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][CH2:9][C:10]1[CH:11]=[C:12]([N:16]2[C:20]3[CH:21]=[CH:22][C:23]([CH:25]=[O:26])=[CH:24][C:19]=3[N:18]=[CH:17]2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 159087TriacetoxyperiodinaneHCID 12001224HCID 12001224, compound

Product 1

HCID 57556918HCID 57556918, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of compound 10a (320 mg, 0.92 mmol) in dry CH2Cl2 (10 mL) in a N2 atmosphere was added Dess-Martin periodinane (DMP) (600 mg) portion wise and the reaction mixture was stirred for 3 hours at RT. The reaction mixture was quenched with solid NaHCO3 at 0° C. The product was extracted with CH2Cl2 (3×30 mL) and the combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using a 3:7 mixture of ethyl acetate and pet-ether as the eluent to afford compound 12a (220 mg) as a gum.

Workup

  1. customThe reaction mixture was quenched with solid NaHCO3 at 0° C
  2. extractionThe product was extracted with CH2Cl2 (3×30 mL)
  3. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel using
  6. additiona 3:7 mixture of ethyl acetate and pet-ether as the eluent

Sources & evidence

ORD record
ord-9aa623121a994b5cb649e066de49b454
Source dataset
uspto-grants-2010_08
Patent number
US07776900B2

Reaction notes

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