Triphenylphosphine → (4S)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-amine

HRID 1009165Notes

Reaction equation

HRID 1009165 reaction equation
[N:1]([C@@H:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:14])[CH:12]=2)[O:7][C:6]([CH3:19])([C:15]([F:18])([F:17])[F:16])[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O>[Br:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[O:7][C:6]([CH3:19])([C:15]([F:16])([F:18])[F:17])[CH2:5][C@@H:4]2[NH2:1]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86614139(4S)-4-azido-6-bromo-2-methyl-2-(trifluoromethyl)chroman

Product 1

HCID 67305954(4S)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (4S)-4-azido-6-bromo-2-methyl-2-(trifluoromethyl)chroman (190 mg, 565 μmol) was added triphenylphosphine (222 mg, 848 μmol). The mixture was stirred at RT for 4 h. Water (15 ml) was added and the reaction was heated at refluxing for 24 h. The resulted mixture was concentrated to dryness and extracted with CHCl3. The organic layer was dried over anhydrous Na2SO4, filtered, concentrated and dried in vacuum to afford the title compound. MS m/z: 293, 295(M−NH2).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat refluxing for 24 h
  3. concentrationThe resulted mixture was concentrated to dryness
  4. extractionextracted with CHCl3
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried in vacuum

Sources & evidence

ORD record
ord-2734968c4a8f4d36bac756ea2a72749e
Source dataset
uspto-grants-2011_07
Patent number
US07973047B2

Reaction notes

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