Triacetoxyperiodinane → methyl 14-cyclohexyl-7-oxo-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 1714012Notes

Reaction equation

HRID 1714012 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:27]([O:29][CH3:30])=[O:28])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][C@@H:16]([OH:26])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOC(C)=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:27]([O:29][CH3:30])=[O:28])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][C:16](=[O:26])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 66674899methyl (7S)-14-cyclohexyl-7-hydroxy-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 50994368methyl 14-cyclohexyl-7-oxo-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl (7S)-14-cyclohexyl-7-hydroxy-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (from Step 3) in DCM (0.1 M) was added Dess-Martin periodinane (DMP, 1.2 eq), and the mixture was stirred for 1 h at RT. At this point another 0.6 eq of DMP were added and the reaction left overnight. The reaction mixture was diluted with EtOAc and washed with an aqueous solution of a 1:1 mixture containing sodium thiosulfate and NaHCO3 (both saturated solutions), then with water and brine. Drying over Na2SO4, filtration and concentration in vacuo gave the crude product, which was used without further purification (90%); MS (ES+) m/z 404 (M+H)+.

Workup

  1. waitthe reaction left overnight
  2. washwashed with an aqueous solution of a 1:1 mixture
  3. additioncontaining sodium thiosulfate and NaHCO3 (both saturated solutions), then with water and brine
  4. dry with materialDrying over Na2SO4, filtration and concentration in vacuo

Sources & evidence

ORD record
ord-c62eed4814c64743886c87d3683e0c97
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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