1,4-Dioxane → (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-formylisoquinolin-3-yl)ethylcarbamate

HRID 1626935Notes

Reaction equation

HRID 1626935 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH:12]=C)=[N:9][C:8]([C@@H:14]([NH:16][C:17](=[O:33])[O:18][CH2:19][CH:20]1[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:26]3[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH3:15])=[CH:7]2.[O:34]1CCOCC1>O.O=[Os](=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH:12]=[O:34])=[N:9][C:8]([C@@H:14]([NH:16][C:17](=[O:33])[O:18][CH2:19][CH:20]1[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=3[C:27]3[C:32]1=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:15])=[CH:7]2

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 69097659HCID 69097659, compound

Product 1

HCID 86677063(S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-formylisoquinolin-3-yl)ethylcarbamate

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

To a suspension of (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-vinylisoquinolin-3-yl)ethylcarbamate (347) (10.6 g, 23.3 mmol, 1.0 eq) in 1,4-dioxane (200 mL) and water (100 mL), OsO4 (50 mg) was added and the resulting mixture was stirred at RT for 30 min. To this mixture, NaIO4 (15 g, 69.9 mmol, 3.0 eq) was added, and then the mixture was stirred at RT for 16 h. The mixture reaction was poured into water (200 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was washed with water (2×100 mL) and brine (100 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (5-20% ethyl acetate-petro ether) to afford (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-l-formylisoquinolin-3-yl)ethylcarbamate (348).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at RT for 16 h
  3. customThe mixture reaction
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe organic layer was washed with water (2×100 mL) and brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel (5-20% ethyl acetate-petro ether)

Sources & evidence

ORD record
ord-12592a70549e4b089ef88d3e430d211d
Source dataset
uspto-grants-2014_07
Patent number
US08785470B2

Reaction notes

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