Hydrogen Peroxide → HCID 66674539, compound

HRID 1714038Notes

Reaction equation

HRID 1714038 reaction equation
B.CSC.[CH:5]1([C:11]2[C:12]3[CH:13]=[CH:14][C:15]([C:31]([O:33][CH3:34])=[O:32])=[CH:16][C:17]=3[N:18]3[C:25]=2[C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[O:22][CH2:21][C:20](=[CH2:30])[CH2:19]3)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[OH-:35].[Na+].OO>C1COCC1.CCOC(C)=O>[CH:5]1([C:11]2[C:12]3[CH:13]=[CH:14][C:15]([C:31]([O:33][CH3:34])=[O:32])=[CH:16][C:17]=3[N:18]3[C:25]=2[C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[O:22][CH2:21][CH:20]([CH2:30][OH:35])[CH2:19]3)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 66674413methyl 14-cyclohexyl-7-methylene-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 66674539HCID 66674539, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Borane-dimethylsulfide complex (2M solution in THF, 1.6 eq) was added to a solution of methyl 14-cyclohexyl-7-methylene-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (from Step 1) in dry THF (0.12 M) at 0° C. The solution was stirred for 16 h at RT. The reaction mixture was cooled to 0° C. and treated dropwise with 3N NaOH (3 eq.) followed by 35% (v/v) H2O2 solution and the resulting mixture was stirred for 2 h at RT. The mixture was diluted with EtOAc, washed with aqueous saturated NaHCO3-solution and with brine, dried (Na2SO4). Evaporation afforded a crude residue which was purified by flash chromatography (4:1 PE/EtOAc). Methyl 14-cyclohexyl-7-(hydroxymethyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (50%) was obtained as colorless solid; MS (ES+) m/z 402 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringthe resulting mixture was stirred for 2 h at RT
  3. washwashed with aqueous saturated NaHCO3-solution and with brine
  4. dry with materialdried (Na2SO4)
  5. customEvaporation
  6. customafforded a crude residue which
  7. customwas purified by flash chromatography (4:1 PE/EtOAc)

Sources & evidence

ORD record
ord-3d348c7e23994bc98b0b1e0bf28e12cf
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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