Water → 6-bromo-1,2,3,4-tetrahydro-2,2-dimethyl-4-Quinolinamine

HRID 1009142노트

반응식

HRID 1009142 반응식
[N:1]([CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:14])[CH:12]=2)[NH:7][C:6]([CH3:16])([CH3:15])[CH2:5]1)=[N+]=[N-].O.C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOC(C)=O>[Br:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:15])([CH3:16])[CH2:5][CH:4]2[NH2:1]

참가 물질

6

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 866141294-Azido-6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 673058276-bromo-1,2,3,4-tetrahydro-2,2-dimethyl-4-Quinolinamine

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-azido-6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (2.29 g, 8.15 mmol), water (6.50 ml, 361 mmol), and THF (20.4 ml, 8.15 mmol) was added triphenylphosphine (2.35 g, 8.96 mmol) in one portion. The resulting mixture was heated to 40 deg C. and stirred overnight. The crude mixture was dissolved with EtOAc and transferred to a sep. funnel containing 0.5 MHCl. The aqueous layer was washed 5×DCM. The aqueous layer was then neutralized with 6N NaOH and washed 3× with EtOAc. The organic layers were combined, dried with MgSO4, filtered and concentrated to provide the desired product. MS m/z: 239 (M−NH2).

후처리

  1. temperatureThe resulting mixture was heated to 40 deg C
  2. additionfunnel containing 0.5 MHCl
  3. washThe aqueous layer was washed 5×DCM
  4. washwashed 3× with EtOAc
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6d10aba2581b4925bf30e773aacdfa7c
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973047B2

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