Water → Benzyl 4-(2-(1-bromo-2,2,2-trifluoroethylidene)hydrazinyl)piperidine-1-carboxylate

HRID 2196551

반응식

HRID 2196551 반응식
[F:1][C:2]([F:23])([F:22])[CH:3]=[N:4][NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1.C1C(=O)N([Br:31])C(=O)C1.C(OCC)(=O)C.O>CN(C=O)C.[Cl-].[Na+].O>[Br:31][C:3](=[N:4][NH:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH2:10][CH2:11]1)[C:2]([F:1])([F:22])[F:23]

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 69095121Benzyl 4-(2-(2,2,2-trifluoroethylidene)hydrazinyl)piperidine-1-carboxylate

생성물 1

HCID 72576664Benzyl 4-(2-(1-bromo-2,2,2-trifluoroethylidene)hydrazinyl)piperidine-1-carboxylate수율 47.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

To a stirred solution of 110 (2.881 g, 8.75 mmol) in DMF (29.2 ml) was added NBS (1.713 g, 9.62 mmol) and the resulting solution was allowed to stir for 1 h at room temperature. Ethyl acetate was added followed by brine and water (50/50), and the AcOEt extracts were washed with water and brine, dried over MgSO4, filtrated and concentrated. The residue was purified via Biotage (5% to 20% EtOAc/Hexane; 25M column) to afford 111 (1.685 g, 47.2% yield) as yellow oil. LRMS (ESI): calc. 407.05 and 409.04; found 408.2 and 410.2 (MH)+.

후처리

  1. washthe AcOEt extracts were washed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltrated
  4. concentrationconcentrated
  5. customThe residue was purified via Biotage (5% to 20% EtOAc/Hexane; 25M column)

출처 및 근거

ORD 기록
ord-1cfab658b86b4bb48a29122423ec33cc
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338437B2

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