Lithium azide → (S)-2-azido-5,7-difluoro-1,2,3,4-tetrahydronaphthalene

HRID 863064Notes

Reaction equation

HRID 863064 reaction equation
CS(O[C@@H:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([F:17])=[CH:11][C:12]=2[F:16])[CH2:7]1)(=O)=O.[N-:18]=[N+:19]=[N-:20].[Li+]>CN(C=O)C>[N:18]([C@H:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([F:17])=[CH:11][C:12]=2[F:16])[CH2:7]1)=[N+:19]=[N-:20]

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 53750897(R)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl methanesulfonate

Product 1

HCID 54273911(S)-2-azido-5,7-difluoro-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (R)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl methanesulfonate (54.0 g), prepared as in Example 7, and lithium azide (15.8 g, 0.322 mol) in 400 mL of DMF was stirred under argon at 50° C. for 16 hours. The reaction was quenched with 200 mL of water and the mixture extracted with 1 L of pentane. The extract was washed with 50 mL of water and dried over magnesium sulfate. Evaporation under reduced pressure at 35° C. gave crude (S)-2-azido-5,7-difluoro-1,2,3,4-tetrahydronaphthalene as a yellow oil residue (59.8 g).

Workup

  1. customThe reaction was quenched with 200 mL of water
  2. extractionthe mixture extracted with 1 L of pentane
  3. washThe extract was washed with 50 mL of water
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation under reduced pressure at 35° C.

Sources & evidence

ORD record
ord-001de6eb45174435a2630172b6164029
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

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