Sodium Azide → HCID 59543137, compound

HRID 1970988Notes

Reaction equation

HRID 1970988 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][CH:9]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH:8]([F:20])[CH2:7]1)(=O)=O.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C.CCOC(C)=O>[N:21]([CH:6]1[CH2:11][CH2:10][CH:9]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH:8]([F:20])[CH2:7]1)=[N+:22]=[N-:23]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 595431564-{[tert-Butyl(dimethyl)silyl]oxy}-3-fluorocyclohexyl methanesulfonate

Product 1

HCID 59543137HCID 59543137, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 4-{[tert-butyl(dimethyl)silyl]oxy}-3-fluorocyclohexyl methanesulfonate (570 mg, 1.75 mmol) in DMF (10 mL) was added sodium azide (340 mg, 5.24 mmol). The reaction mixture was heated to 100° C. overnight, diluted with EtOAc, and washed with water. The organic layer was dried, concentrated, and purified by flash chromatography to afford the title compound.

Workup

  1. washwashed with water
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8b2a9d2461814b968369fa408eeedb35
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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