tert-Butyl piperazine-1-carboxylate → HCID 178452249、化合物

HRID 2206327ノート

反応式

HRID 2206327 の反応式
Cl[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=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>CCCCO.CCOC(C)=O>[OH:8][C:6]1[CH:5]=[CH:4][N:3]=[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]=1

参加物

5

反応物 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 178516507HCID 178516507、化合物

生成物 1

HCID 178452249HCID 178452249、化合物収率 44%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

To a solution of 2-chloro-4-hydroxypyridine (12.9 g, 100 mmol) in n-BuOH (50 mL) was added t-butyl piperazine-1-carboxylate (46.5 g, 250 mmol). The mixture was heated at 140° C. for 3 days and then diluted with EtOAc (2 L) at ambient temperature. The organic phase was washed with saturated NH4Cl solution and then brine. The organic layer was separated, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography (5%-20% MeOH/CH2Cl2) to give 12.2 g (44%) of t-butyl 4-(4-hydroxypyridin-2-yl)piperazine-1-carboxylate as a white solid. MS m/z 280.2 [M+H]+; 1H NMR (500 MHz, CDCl3) δ (ppm) 7.72 (1H, d, J=6.62 Hz), 6.20 (1H, dd, J=6.31, 2.21 Hz), 6.02 (1H, d, J=1.89 Hz), 3.56 (4H, m), 3.42 (4H, m), 1.50 (9H, s).

後処理

  1. washThe organic phase was washed with saturated NH4Cl solution
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (5%-20% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-8c6c19d3e1d641d3ad7b9405c9cfb760
出典データセット
uspto-grants-2016_06
特許番号
US09371336B2

反応ノート

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