Sodium Azide → Benzyl 4-(azidomethyl)-4-fluoropiperidine-1-carboxylate

HRID 1827240Notes

Reaction equation

HRID 1827240 reaction equation
[F:1][C:2]1([CH2:18]OS(C)(=O)=O)[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C>[N:24]([CH2:18][C:2]1([F:1])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1)=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22135556Benzyl 4-fluoro-4-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate

Product 1

HCID 22135652Benzyl 4-(azidomethyl)-4-fluoropiperidine-1-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of benzyl 4-fluoro-4-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate (1.3 g, 3.7 mmol) in DMF (10 mL) at RT was added NaN3 (2.4 g, 37.0 mmol). The reaction mixture was heated to 110° C. and stirred for 60 h, cooled and partitioned between EtOAc and H2O. The organic layer was dried over Na2SO4, filtered, concentrated and purified on silica gel (10:1 to 1:2 hexanes:EtOAc) to give benzyl 4-(azidomethyl)-4-fluoropiperidine-1-carboxylate. (0.86 g, 80% yield). M.S. (M+1): 293

Workup

  1. temperaturecooled
  2. custompartitioned between EtOAc and H2O
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel (10:1 to 1:2 hexanes:EtOAc)

Sources & evidence

ORD record
ord-eefe7973dc804bcd8b26b27a808afb53
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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