Hydrogen Peroxide → Methyl 14-cyclohexyl-5-hydroxy-5,6,7,8-tetrahydroindolo[2,1-a][2]benzazocine-11-carboxylate

HRID 1714046Notes

Reaction equation

HRID 1714046 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:26]([O:28][CH3:29])=[O:27])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][CH:19]=[CH:18][C:17]4[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:30].[Na+].OO>C1COCC1>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:26]([O:28][CH3:29])=[O:27])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][CH2:19][CH:18]([OH:30])[C:17]4[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 68505449HCID 68505449, compound

Product 1

HCID 44155800Methyl 14-cyclohexyl-5-hydroxy-5,6,7,8-tetrahydroindolo[2,1-a][2]benzazocine-11-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

BH3Me2S (1.6 eq, 2M solution in THF) was added to a 0.2M solution of methyl 14-cyclohexyl-7,8-dihydroindolo[2,1-a][2]benzazocine-11-carboxylate in THF, and the mixture was stirred for 2 h at RT. 3M aq NaOH (3 eq) and 35% H2O2 (3 eq) were added at 0° C., and stirring was continued overnight at RT. After dilution with sat NaHCO3 the aq. phase was extracted with EtOAc, the organic phase was washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give mainly methyl 14-cyclohexyl-5-hydroxy-5,6,7,8-tetrahydroindolo[2,1-a][2]benzazocine-11-carboxylate (with traces of its regioisomer methyl 14-cyclohexyl-6-hydroxy-5,6,7,8-tetrahydroindolo[2,1-a][2]benzazocine-11-carboxylate).

Workup

  1. stirringstirring
  2. waitwas continued overnight at RT
  3. extractionAfter dilution with sat NaHCO3 the aq. phase was extracted with EtOAc
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4fd2254b9ce4c0c9d2e3b130c06a432
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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