Sodium Azide → HCID 59598465, compound

HRID 2266251Notes

Reaction equation

HRID 2266251 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)=[C:6]([CH:15]([O:29][CH2:30][CH2:31]OS(C)(=O)=O)[C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)[CH:5]=[CH:4][CH:3]=1.[N-:37]=[N+:38]=[N-:39].[Na+]>CN(C=O)C.CCOC(C)=O.O>[N:37]([CH2:31][CH2:30][O:29][CH:15]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=1)[C@@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[CH2:17]1)=[N+:38]=[N-:39]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 59598475HCID 59598475, compound

Product 1

HCID 59598465HCID 59598465, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

(3R)-tert-butyl 3-((6-fluoro-3′-methylbiphenyl-2-yl)(2-(methanesulfonyloxy)ethoxy)methyl)piperidine-1-carboxylate (1.1 g, 2 mmol) was dissolved in anhydrous DMF (15 mL), solid NaN3 (280 mg, 4 mmol) was added and the reaction mixture was heated to 80° C. for 5 h. The mixture was cooled to rt and diluted with EtOAc and water. The organic phase was separated, washed with water and dried over MgSO4. Removal of the solvent gave (3R)-tert-butyl 3-((2-azidoethoxy)(6-fluoro-3′-methylbiphenyl-2-yl)methyl)piperidine-1-carboxylate (0.89 g, yield 90%) which was used in the next step without purification.

Workup

  1. temperatureThe mixture was cooled to rt
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-8d1b23affe79441199b5e174290c75b0
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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