2-Bromoethyldimethylamine → HCID 67036842、化合物

HRID 216072ノート

反応式

HRID 216072 の反応式
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.Br[CH2:28][CH2:29][N:30]([CH3:32])[CH3:31]>C1COCC1>[CH3:31][N:30]([CH3:32])[CH2:29][CH2:28][C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2][N:1]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:6][CH2:5]1

参加物

5

反応物 3

HCID 178642-BromoethyldimethylamineHCID 2724682Lithium diisopropylamideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

生成物 1

HCID 67036842HCID 67036842、化合物収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (514 mg, 2 mmol) in THF (10 mL) at −78° C. was added dropwise LDA (1.5 M in cyclohexane, 2 mL, 3 mmol). After stirring for 30 minutes, 2-bromo-N,N-dimethylethanamine (370 mg, 2.4 mmol) in THF (3 mL) was added. The reaction was stirred for 30 min at −78° C., then allowed to warm to room temperature, stirred for 2 hours, then quenched with sat. aq. NaHCO3, diluted with EtOAc, washed with sat. aq. NaHCO3 and brine (with back extraction), dried over MgSO4, and concentrated under vacuum. The residue was purified by flash chromatography (40 g SiO2, 0-15% MeOH:CH2Cl2) to give the title compound (328 mg, 1.0 mmol, 50%) as a yellow oil. MS (ES+) [M+H]+=329.

後処理

  1. stirringThe reaction was stirred for 30 min at −78° C.
  2. stirringstirred for 2 hours
  3. customquenched with sat. aq. NaHCO3
  4. additiondiluted with EtOAc
  5. washwashed with sat. aq. NaHCO3 and brine (with back extraction)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash chromatography (40 g SiO2, 0-15% MeOH:CH2Cl2)

出典と根拠

ORDレコード
ord-a6aed3f2900b471d8fa8076e5baf4f9d
出典データセット
uspto-grants-2012_06
特許番号
US08193202B2

反応ノート

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