Sodium Sulfite → methyl 3-cyclohexyl-2-(1,2-dihydroxyethyl)-1-[2-(dimethylamino)-2-oxoethyl]-1H-indole-6-carboxylate

HRID 1713942Notes

Reaction equation

HRID 1713942 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])C=2C=C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[N+]1([O-])CC[O:32]CC1.S([O-])([O-])=O.[Na+].[Na+].C1COCC1.[CH3:47][C:48]([CH3:50])=[O:49]>O.[Os](=O)(=O)(=O)=O>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:47]=2[CH:48]([OH:49])[CH2:50][OH:32])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 22559816Acetone tetrahydrofuranHCID 68437081methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-vinyl-1H-indole-6-carboxylate

Product 1

HCID 68433910methyl 3-cyclohexyl-2-(1,2-dihydroxyethyl)-1-[2-(dimethylamino)-2-oxoethyl]-1H-indole-6-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent4×

Procedure

To a solution of methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-vinyl-1H-indole-6-carboxylate (from Step 2) in THF/acetone (0.2 M, 1:1, v:v) was added N-methyl morpholine N-oxide (1.2 eq.). To the resulting suspension water was added (1 volume part), followed by a solution of osmium tetroxide in water (0.1 eq., 4% solution). The resulting solution was left stirring overnight at RT. After one night a saturated solution of sodium sulfite in water was added and the mixture was left stirring for 30 min. The solution was diluted with water and extracted with DCM (3×) and EtOAc (2×). The combined organic extracts were dried over Na2SO4 and evaporated in vacuo. The residual material was dissolved in DCM and precipitated with PE. The product was obtained as a greyish foam (91%).

Workup

  1. waitThe resulting solution was left
  2. waitthe mixture was left
  3. stirringstirring for 30 min
  4. extractionextracted with DCM (3×) and EtOAc (2×)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. customevaporated in vacuo
  7. dissolutionThe residual material was dissolved in DCM
  8. customprecipitated with PE

Sources & evidence

ORD record
ord-a6d9e25242c4479abfe90e9e5d267465
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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