1,8-Diazabicyclo(5.4.0)undec-7-ene → (4S)-4-azido-6-bromo-2-methyl-2-(trifluoromethyl)chroman

HRID 20056Notes

Reaction equation

HRID 20056 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:16])([C:12]([F:15])([F:14])[F:13])[CH2:6][C@H:5]2O.C1(P([N:32]=[N+:33]=[N-:34])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O>[N:32]([C@@H:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[O:8][C:7]([CH3:16])([C:12]([F:15])([F:14])[F:13])[CH2:6]1)=[N+:33]=[N-:34]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 67305384(4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol

Product 1

HCID 86614139(4S)-4-azido-6-bromo-2-methyl-2-(trifluoromethyl)chroman

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled (ice bath) solution of (4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol (277 mg, 890 μmol) was added drop wise diphenylphosphoryl azide (249 μl, 1158 μmol). After stirring 20 min, 1,8-diazabicyclo(5.4.0)undec-7-ene (173 μl, 1158 μmol) was added drop wise. The reaction was stirred at the same temperature for 2 h, then stirred 15h at ambient temperature. Water was added to quench the reaction. The resulted mixture was extracted with EtOAc. The organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified on a silica gel column (5-20% EtOAc/hexane) to afford the title compound. MS m/z: 308(M−N2).

Workup

  1. stirringThe reaction was stirred at the same temperature for 2 h
  2. customto quench
  3. customthe reaction
  4. extractionThe resulted mixture was extracted with EtOAc
  5. washThe organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on a silica gel column (5-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-8996e03614cb4c569905e641b2a98f5b
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Reaction notes

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