Cyanogen Bromide → 4-Methyl-4-phenyl-4,5-dihydro-oxazol-2-ylamine

HRID 1911500Notes

Reaction equation

HRID 1911500 reaction equation
[NH2:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].[N:18]#[C:19]Br>C1COCC1>[CH3:5][C:2]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:3][O:4][C:19]([NH2:18])=[N:1]1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 3497332-Amino-2-phenylpropan-1-ol

Product 1

HCID 593238034-Methyl-4-phenyl-4,5-dihydro-oxazol-2-ylamineYield 65.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred, cooled (0° C.) mixture of 2-amino-2-phenyl-propan-1-ol (266 mg) and K2CO3 (292 mg) in THF (5 ml) under an argon atmosphere was added a solution of cyanogen bromide (292 mg) in THF (5 ml). The ice bath was removed and stirring at r.t. was continued for 18 h. The mixture (white suspension) was taken up in EtOAc/H2O 1:1. The aqueous phase was back extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give 4-methyl-4-phenyl-4,5-dihydro-oxazol-2-ylamine (204 mg) as white solid. MS (ISP): 177.1 ([M+H]+)

Workup

  1. temperatureTo a stirred, cooled
  2. customThe ice bath was removed
  3. extractionThe aqueous phase was back extracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-74eb45af6f134007bc567d86f57f454e
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

Loading…