Sodium Azide → HCID 86598914, compound

HRID 456761Notes

Reaction equation

HRID 456761 reaction equation
CS(O[C@H:6]1[C@H:11]2[CH2:12][C@H:8]([C@@H:9]([C:20]([O:22][CH3:23])=[O:21])[N:10]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]1)(=O)=O.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C)C=O.O.C(OCC)(=O)C>[N:24]([C@H:6]1[C@H:11]2[CH2:12][C@H:8]([C@@H:9]([C:20]([O:22][CH3:23])=[O:21])[N:10]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]1)=[N+:25]=[N-:26]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 86598913HCID 86598913, compound

Product 1

HCID 86598914HCID 86598914, compoundYield 88.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-tert-butyl 3-methyl (1R,3S,4S,6R)-6-[(methylsulfonyl)oxy]-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate obtained in Example 29-1 (232 mg) in dimethylformamide (2.0 mL) and water (0.4 mL), was added sodium azide (108 mg). The mixture was stirred at 80° C. for 1 hr. The resulting mixture was diluted with ethyl acetate, and washed successively with water and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane and ethyl acetate (4:1) to give the target compound (175 mg).

Workup

  1. washwashed successively with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-18540e554205493a859b34d03fb8c8ef
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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