Sodium Sulfite → HCID 68506124, compound

HRID 1714047Notes

Reaction equation

HRID 1714047 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]CC=C[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.C[N+]1([O-])CC[O:34]CC1.[O-]S([O-])=O.[Na+].[Na+].[CH3:44][C:45]([CH3:47])=[O:46].C1COCC1.O>O.O=[Os](=O)(=O)=O>[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][CH2:47][CH:45]([OH:46])[CH:44]([OH:34])[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

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 21553975Acetone water tetrahydrofuranHCID 68505449HCID 68505449, compound

Product 1

HCID 68506124HCID 68506124, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

A solution (0.11 M) of methyl 14-cyclohexyl-7,8-dihydroindolo[2,1-a][2]benzazocine-11-carboxylate (prepared as in Example 41, Step 3) in acetone/THF/H2O (1/1/1) was treated with N-methylmorpholine-N-oxide (1.2 eq), followed by OsO4 (4% wt in H2O, 0.1 eq) and left stirring at RT overnight. The clear solution was then treated with 10% wt Na2SO3 and left stirring for 30 min, then diluted with H2O and extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4 and evaporated i. vac. to give the clean title compound as a creamy solid; MS (ES+) m/z 420 (M+H)+.

Workup

  1. waitleft
  2. waitleft
  3. stirringstirring for 30 min
  4. extractionextracted with EtOAc
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated i

Sources & evidence

ORD record
ord-13337eeda0ad438098caf2749cc98999
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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