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

HRID 1911500노트

반응식

HRID 1911500 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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]+)

후처리

  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)

출처 및 근거

ORD 기록
ord-74eb45af6f134007bc567d86f57f454e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604061B2

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