Water → HCID 86696727, compound

HRID 1774227Notes

Reaction equation

HRID 1774227 reaction equation
C[O:2][N+]1(C)CCOCC1.[CH:10]([C:12]1[N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH2:11].[O-]S([O-])=O.[Na+].[Na+].[OH2:34]>CC(C)=O.C1COCC1.O=[Os](=O)(=O)=O>[OH:34][CH:10]([C:12]1[N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][OH:2]

Participants

8

Reactant 4

HCID 962Water2×HCID 24437Sodium SulfiteHCID 20812268HCID 20812268, compoundHCID 86696726HCID 86696726, compound

Product 1

HCID 86696727HCID 86696727, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Methoxy-4-methylmorpholin-4-ium (1.5 g, 12.8 mmol), water (10 mL), and OsO4 (250 mg, 1 mmol) in water (10 mL) were added to a mixture of tert-butyl 2-vinyl-1H-indole-1-carboxylate (2.60 g, 10.7 mmol) in acetone (15 mL) and THF (15 mL). After being stirred at room temperature for 16 hours, saturated Na2SO3 was added, and the resulting mixture was stirred for 30 minutes. The insoluble material was filtered off. The filtrate was extracted with ethyl acetate (2×100 mL), washed with brine, dried, and concentrated to give tert-butyl 2-(1,2-dihydroxyethyl)-1H-indole-1-carboxylate (2.0 g, 69% yield) as an oil.

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. filtrationThe insoluble material was filtered off
  3. extractionThe filtrate was extracted with ethyl acetate (2×100 mL)
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b872b287097244d99e998fa5ae65b9e4
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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