Ytterbium triflate → HCID 68979684, compound

HRID 2035421Notes

Reaction equation

HRID 2035421 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]([CH3:11])[C:4]=2[CH:3]=1.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.CO/[CH:45]=[CH:46]/[C:47]([O:49][Si](C)(C)C)=[CH2:48]>>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]3[CH:45]=[CH:46][C:47](=[O:49])[CH2:48][CH:7]3[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]([CH3:11])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 2733225Ytterbium triflateHCID 5366448trans-1-Methoxy-3-trimethylsilyloxy-1,3-butadieneHCID 68976360HCID 68976360, compound

Product 1

HCID 68979684HCID 68979684, compoundYield 41%

Procedure

To a stirred solution of 2-bromo-11-methyl-11H-dibenzo[b,e]azepine (5R8═Br; 666 mg, 2.33 mmol) ytterbium (III)triflate (146 mg, 0.23 mmol) was added. After stirring for 10 min. at room temperature Danishefsky's diene (0.89 mL, 4.66 mmol) was added. The reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was quenched with aqueous NaHCO3, extracted into ethyl acetate, washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica to give 8-bromo-10,14b-dihydro-10-methyl-dibenzo[c,f]pyrido[1,2-a]azepin-2(1H)-one (6, R8═Br; 338 mg, 41%). Data: (m/z)=354/356 (M+H)+.

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with aqueous NaHCO3
  3. extractionextracted into ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica

Sources & evidence

ORD record
ord-b8f7dbe80a3a4e43a4d2cbb88b61774d
Source dataset
uspto-grants-2013_11
Patent number
US08575152B2

Reaction notes

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