Sodium hydride → Tert-butyl 3-bromo-2-oxo-1,4'-bipiperidine-1'carboxylate

HRID 407895ノート

反応式

HRID 407895 の反応式
[Br:1][CH:2]([CH2:19][CH2:20][CH2:21]Br)[C:3]([NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:4].[H-].[Na+]>CN(C=O)C>[Br:1][CH:2]1[CH2:19][CH2:20][CH2:21][N:5]([CH:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[C:3]1=[O:4]

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 67469892Tert-butyl 4-(2,5-dibromopentanamido)piperidine-1-carboxylate

生成物 1

HCID 86688083Tert-butyl 3-bromo-2-oxo-1,4'-bipiperidine-1'carboxylate収率 75%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of tert-butyl 4-(2,5-dibromopentanamido)piperidine-1-carboxylate (2.21 g, 5.00 mmol) dissolved in DMF (10 mL) was added 60% sodium hydride (0.220 g, 5.5 mmol). The reaction was allowed to stir for 2 hours and then concentrated under vacuum. The resulting material was diluted with water and EtOAc. The organic layer was separated and the aqueous layer washed with EtOAc. The combined organic layers were dried with MgSO4 and concentrated. The residue was purified over silica gel (2:1 hexanes:EtOAc) to give tert-butyl 3-bromo-2-oxo-1,4′-bipiperidine-1′carboxylate (1.35 g, 75%) as a white solid.

後処理

  1. concentrationconcentrated under vacuum
  2. additionThe resulting material was diluted with water and EtOAc
  3. customThe organic layer was separated
  4. washthe aqueous layer washed with EtOAc
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified over silica gel (2:1 hexanes:EtOAc)

出典と根拠

ORDレコード
ord-1b18eb7582fa4a929373e9c415b63740
出典データセット
uspto-grants-2014_06
特許番号
US08754226B2

反応ノート

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