1,4-Dioxane → HCID 86686145, compound

HRID 869199Notes

Reaction equation

HRID 869199 reaction equation
[F:1][C:2]1[C:3]([C:8]2([CH2:12][N:13]([C:21]3[N:22]=[N:23][C:24]([CH:27]=C)=[CH:25][CH:26]=3)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[O:29]1CCOCC1.I([O-])(=O)(=O)=O.[Na+]>O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[C:3]([C:8]2([CH2:12][N:13]([C:21]3[N:22]=[N:23][C:24]([CH:27]=[O:29])=[CH:25][CH:26]=3)[C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 23667635Sodium periodateHCID 86686144HCID 86686144, compound

Product 1

HCID 86686145HCID 86686145, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

t-Butyl (1-(3-fluoropyridin-2-yl)cyclobutyl)methyl(6-vinylpyridazin-3-yl)carbamate (3.4 g, 8.84 mmol) was added as a dioxane (100 mL) solution to a mixture of sodium periodate (10.8 g, 50.5 mmol) and 4% osmium tetraoxide solution (6.5 mL) in H2O (30 mL) at 0° C. The reaction was stirred for 2 h. The reaction mixture was filtered through a pad of celite and washed with EtOAc. The organic layer was washed with satd. aq. NaHCO3, brine and dried over sodium sulfate, filtered, and concentrated. Silica gel chromatography provided a colorless oil (1.4 g, 41%), (m/z [M+H]=387.2).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashed with EtOAc
  3. washThe organic layer was washed with satd
  4. dry with materialaq. NaHCO3, brine and dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6d51200ce78a40dfbc23ba6373bfbdfa
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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