Water → 1,1-Dimethylethyl (3S)-3-(azidomethyl)-3-fluoro-1-piperidinecarboxylate

HRID 473331Notes

Reaction equation

HRID 473331 reaction equation
[F:1][C@@:2]1([CH2:15]OS(C(F)(F)F)(=O)=O)[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[N-:24]=[N+:25]=[N-:26].[Na+].CC(OC)(C)C.O>CN(C=O)C>[N:24]([CH2:15][C@:2]1([F:1])[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1)=[N+:25]=[N-:26]

Participants

6

Reactant 4

HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 33557Sodium AzideHCID 866767991,1-dimethylethyl (3S)-3-fluoro-3-({[(trifluoromethyl)sulfonyl]oxy}methyl)-1-piperidinecarboxylate

Product 1

HCID 866768001,1-Dimethylethyl (3S)-3-(azidomethyl)-3-fluoro-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

1,1-Dimethylethyl (3S)-3-fluoro-3-({[(trifluoromethyl)sulfonyl]oxy}methyl)-1-piperidinecarboxylate (1 wt) is dissolved in N,N,-dimethylformamide (3 vol) at 20° C. and sodium azide (1.1 eq, 0.20 wt) is added. The resulting suspension is stirred at 20-30° C. for 6 h. TBME (5 vol) and water (9 vol) are added. The mixture is stirred for 5 min and the layers are separated. The aqueous phase is extracted with TBME (5 vol) and the TBME phases are combined. The combined organics are washed with water (2×5 vol), filtered and concentrated under reduced pressure to give the title compound as an orange oil.

Workup

  1. stirringThe mixture is stirred for 5 min
  2. customthe layers are separated
  3. extractionThe aqueous phase is extracted with TBME (5 vol)
  4. washThe combined organics are washed with water (2×5 vol)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f196da54148459595974240aa91cdfd
Source dataset
uspto-grants-2014_01
Patent number
US08633319B2

Reaction notes

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