Sodium Azide → (1R*,2R*,5R*)-8-(4-Azidobut-2-ynyl)-2-{[3,5-bis(trifluoromethyl)phenyl]-methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088112Notes

Reaction equation

HRID 2088112 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@@H:15]2[CH2:21][CH2:20][C@@H:19]3[N:22]([CH2:23][C:24]#[C:25][CH2:26]Cl)[C@@:16]2([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:17][CH2:18]3)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[N-:36]=[N+:37]=[N-:38].[Na+]>CN(C)C=O.O>[N:36]([CH2:26][C:25]#[C:24][CH2:23][N:22]1[C@@H:19]2[CH2:18][CH2:17][C@@:16]1([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@H:15]([O:14][CH2:13][C:5]1[CH:4]=[C:3]([C:2]([F:35])([F:34])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=1)[CH2:21][CH2:20]2)=[N+:37]=[N-:38]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86586646(1R*,2R*,5R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-8-(4-chlorobut-2-ynyl)-1-phenyl-8-azabicyclo[3.2.1]octane

Product 1

HCID 86586648(1R*,2R*,5R*)-8-(4-Azidobut-2-ynyl)-2-{[3,5-bis(trifluoromethyl)phenyl]-methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(1R*,2R*,5R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-8-(4-chlorobut-2-ynyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Description 26; 254 mg, 0.49 mmol) and sodium azide (35 mg, 0.54 mmol) were stirred in dimethylformamide (3 ml) at room temperature overnight. The reaction mixture was diluted with water and the product extracted with ethyl acetate (×3), dried (MgSO4) and concentrated in vacuo to give the title compound as an orange oil.

Workup

  1. extractionthe product extracted with ethyl acetate (×3)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8e1af85e0364b6791dcd0d9aedc7161
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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