tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate

HRID 2403569

反応式

HRID 2403569 の反応式
Br[C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[Na].CC(O)(C)C>C1(C)C=CC=CC=1>[CH3:8][C:3]1[C:2]([N:12]2[CH2:11][CH2:10][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13]2)=[CH:7][CH:6]=[CH:5][N:4]=1

参加物

5

反応物 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 12010033-Bromo-2-methylpyridineHCID 45051916Sodium tert-butoxide

生成物 1

HCID 68106327Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate収率 98%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

3-Bromo-2-methylpyridine (500 mg) and tert-butyl piperazine-1-carboxylate (650 mg) were dissolved in toluene (7.5 ml), and (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one_palladium (3:2) (40 mg), 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine) (18 mg), and 2-methylpropan-2-ol sodium (391 mg) were added thereto in this order under a nitrogen atmosphere, followed by warming to 100° C. and stirring overnight. The reaction mixture was subjected to liquid separation with CHCl3 and water, the organic layer was dried over Na2SO4, and then the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (CHCl3 to 5% MeOH/CHCl3) to obtain tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate (790 mg) as a pale yellow oil.

後処理

  1. customThe reaction mixture was subjected to liquid separation with CHCl3 and water
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe obtained residue was purified by silica gel column chromatography (CHCl3 to 5% MeOH/CHCl3)

出典と根拠

ORDレコード
ord-98cadd563f1c443daa2dfa7faf16755c
出典データセット
uspto-grants-2014_08
特許番号
US08802679B2

関連ノート

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