Benzyl Bromide → 1-tert-Butyl 4-ethyl 4-benzylpiperidine-1,4-dicarboxylate

HRID 862189ノート

反応式

HRID 862189 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:15][C:16]([CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)=[O:17])[CH3:14].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1.C(OCC)(=O)C>[CH2:13]([O:15][C:16]([C:18]1([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:20][CH2:19]1)=[O:17])[CH3:14]

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 178418339Butyllithium

生成物 1

HCID 162182711-tert-Butyl 4-ethyl 4-benzylpiperidine-1,4-dicarboxylate収率 110.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a stirring solution of diisopropyl amine (38.0 mmol, 3.84 g) in THF (50 mL) cooled to -78° C. was added n-butyl lithium dropwise (41.2 mmol, 16.5 mL of a 1.6M solution in hexanes). To this was added piperidine-1,4-dicarboxylic acid tert-butyl ester ethyl ester (31.7 mmol, 8.16 g) in 20 mL THF. The reaction was allowed to stir for 5 min. and benzyl bromide (31.7 mmol, 5.42 g) was added. The reaction was then allowed to warm to room temperature. The reaction was then diluted with ethyl acetate (200 mL) and washed with 10% KHSO4. The aqueous layers were extracted with ethyl acetate (100 mL). The organics were combined, washed with brine and dried over anhydrous sodium sulfate. The solution was filtered and evaporated under reduced pressure to give 12.13 g of the title compound as a yellow oil.

後処理

  1. washwashed with 10% KHSO4
  2. extractionThe aqueous layers were extracted with ethyl acetate (100 mL)
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe solution was filtered
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-6375f2715dde4a28ac8a75d35481e0fe
出典データセット
uspto-grants-1998_02
特許番号
US05717100

反応ノート

読み込み中…