Sodium Azide → (3R,7R)-3-Azido-7-phenylazepan-2-one

HRID 1271471Notes

Reaction equation

HRID 1271471 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH:6]1[CH2:12][CH2:11][CH2:10][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:8][C:7]1=[O:19]>CN(C)C=O>[N:1]([C@@H:6]1[CH2:12][CH2:11][CH2:10][C@H:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:8][C:7]1=[O:19])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 140034323-Bromo-7-phenyl-hexahydroazepin-2-one

Product 1

HCID 14003441(3R,7R)-3-Azido-7-phenylazepan-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium azide (8.73 g, 134 mmol) was added to a solution of 3-bromo-7-phenylazepan-2-one in N,N-dimethylformamide (40 mL) and the mixture heated to 60° C. After 2 h the reaction was allowed to cool to ambient temperature, concentrated, and diluted with water. The mixture was extracted with ethyl acetate, and the organic layer was washed with water (3×) and saturated brine, dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (30% ethyl acetate/hexanes→50% ethyl acetate/hexanes) gave the racemic cis and trans compounds. The cis enantiomers were separated on a Chiralpak AD column eluting with 100% methanol to give the title compound (1.09 g). MS 231 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationconcentrated
  3. additiondiluted with water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water (3×) and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (30% ethyl acetate/hexanes→50% ethyl acetate/hexanes)
  10. customgave the racemic cis and trans compounds
  11. customThe cis enantiomers were separated on a Chiralpak AD column
  12. washeluting with 100% methanol

Sources & evidence

ORD record
ord-347b3da9af8c4f529efd9dfe783b6d15
Source dataset
uspto-grants-2007_04
Patent number
US07205292B2

Reaction notes

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