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

HRID 20057Notes

Reaction equation

HRID 20057 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-049fc0c682a2499bb5ec62fcbcf58964
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Reaction notes

Loading…