Sodium Azide → HCID 86624151, compound

HRID 602472Notes

Reaction equation

HRID 602472 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10](OS(C)(=O)=O)[CH2:9][N:8]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:2].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:25]([C@@H:10]1[CH2:9][N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:24])[CH2:11]1)=[N+:26]=[N-:27]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86624150HCID 86624150, compound

Product 1

HCID 86624151HCID 86624151, compoundYield 149.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of tert-butyl (2R,4R)-2-(3-ethoxy-3-oxopropyl)-4-[(methylsulfonyl)oxy]pyrrolidine-1-carboxylate (462 mg, 1.20 mmol, step 3 of Example 8) and sodium azide (228 mg, 3.5 mmol) in N,N-dimethylformamide (10 mL) was stirred at 80° C. for 14 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (150 mL), washed with water (50 mL×2) and brine (50 mL). The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure to give 562 mg (100%) of the title compound as a colorless oil, which was used for the next step without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (50 mL×2) and brine (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd21d21ddc4c4b14b40d55627745155b
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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