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

HRID 2196551

反応式

HRID 2196551 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-1cfab658b86b4bb48a29122423ec33cc
出典データセット
uspto-grants-2012_12
特許番号
US08338437B2

関連ノート

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