Sodium Azide → HCID 86590310, compound

HRID 1624277Notes

Reaction equation

HRID 1624277 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@@H:12](Cl)[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C.[Cl-].[Na+].O.C(OCC)(=O)C.O>[N:16]([C@H:12]1[CH2:13][CH2:14][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:10]=[CH:11]1)=[N+:17]=[N-:18]

Participants

7

Reactant 2

HCID 33557Sodium AzideHCID 69296253HCID 69296253, compound

Product 1

HCID 86590310HCID 86590310, compoundYield 60%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of cis-1-(tert-butoxycarbonylamino)-4-chloro-2-cyclohexene (1.85 g, 8.00 mmol) in DMF (40 mL) was added sodium azide (1.17 g, 18.0 mmol) and the resultant mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into brine (40 mL) and diluted with ethyl acetate (120 mL) and water (20 mL). The phases were separated and the organic phase was washed with brine (4×25 mL). The organic phase was dried (MgSO4), and concentrated. Purification of the crude material by column chromatography on silica gel (10:1 hexanes-ethyl acetate) provided 1.14 g (60%) of trans-1-azido-4-(tert-butoxycarbonylamino)-2-cyclohexene as a colorless oil.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with brine (4×25 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification of the crude material by column chromatography on silica gel (10:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-56c3748db6d44c18a8cdc872ef0e01dd
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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