Triphenylphosphine → (S)-2-phenyl-1-(thiazol-2-yl)ethanamine

HRID 133802Notes

Reaction equation

HRID 133802 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1([CH2:26][C@H:27]([N:33]=[N+]=[N-])[C:28]2[S:29][CH:30]=[CH:31][N:32]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[NH4+]>O1CCCC1.O>[C:20]1([CH2:26][C@H:27]([NH2:33])[C:28]2[S:29][CH:30]=[CH:31][N:32]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 14923Ammonium HydroxideHCID 10955374(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylazide

Product 1

HCID 10198148(S)-2-phenyl-1-(thiazol-2-yl)ethanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

To a 55° C. (oil bath) solution of triphenylphosphine (1.6 g, 6.3 mmol) in tetrahydrofuran (10 mL) is added (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylazide (contaminated with DPPA, 1.2 g, 5.2 mmol) as a solution in tetrahydrofuran (10 mL). The reaction mixture is allowed to stir for 2 hours at this temperature when aqueous ammonium hydroxide (14 mL) is added. Stirring at 55° C. is continued for 3 hours before the reaction mixture is stored in a −5° C. freezer overnight. The next morning, the reaction mixture is diluted with water (80 mL) and extracted twice with diethyl ether. The combined extracts are washed with 10% aqueous hydrochloric acid (70 mL). The acidic aqueous phase is cooled in an ice-water bath and then basified with 10% aqueous sodium hydroxide to pH 12. The basic phase is then extracted thrice with dichloromethane. The combined extracts are dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to provide a 0.67 g (52% over 2 steps) of a slightly blond oil. MS (ES+): (M+H)=205.0

Workup

  1. additionis added
  2. waitis stored in a −5° C. freezer overnight
  3. extractionextracted twice with diethyl ether
  4. washThe combined extracts are washed with 10% aqueous hydrochloric acid (70 mL)
  5. temperatureThe acidic aqueous phase is cooled in an ice-water bath
  6. extractionThe basic phase is then extracted thrice with dichloromethane
  7. dry with materialThe combined extracts are dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto provide a 0.67 g (52% over 2 steps) of a slightly blond oil

Sources & evidence

ORD record
ord-22f592417bfc4f64b84936284a9a8312
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Reaction notes

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