Water → HCID 59861752, compound

HRID 1010890Notes

Reaction equation

HRID 1010890 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[CH2:17])=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[OH2:19].C[N+]1([O-])CCOCC1.S([O-])([O-])=O.[Na+].[Na+].[OH2:34]>CC(C)=O.[Os](=O)(=O)(=O)=O>[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([OH:34])[CH2:17][OH:19])=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 59861741HCID 59861741, compound

Product 1

HCID 59861752HCID 59861752, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

485 mg of the compound [5-1] was dissolved in a mixed solvent of 18 mL of acetone and 3 mL of water, then 460 mg of 4-methylmorpholine 4-oxide monohydrate and 590 μL of osmium tetroxide (0.1M aqueous solution) were added in that order, and the mixture was stirred overnight at room temperature. 10 mL of 10% aqueous solution of sodium sulfite was added thereto, and after the 30 minutes stirring, the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-0/100), to obtain 351 mg of tert-butyl{(1S)-1-[4-(1,2-dihydroxyethyl) phenyl]ethyl}carbamate [7-1] (hereinafter, referred to as the compound [7-1]) as a colorless oily product.

Workup

  1. stirringafter the 30 minutes stirring
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-0/100)

Sources & evidence

ORD record
ord-f0c4343f55604f1992949c4e2fce54e3
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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