Phosphorus oxychloride → Tert-butyl 4-(4-cyanophenyl)-3,6-dihydropyridine-1(2h)-carboxylate

HRID 541180ノート

反応式

HRID 541180 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2(O)[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 59003435Tert-butyl 4-(4-cyanophenyl)-4-hydroxypiperidine-1-carboxylate2 回

生成物 1

HCID 11289112Tert-butyl 4-(4-cyanophenyl)-3,6-dihydropyridine-1(2h)-carboxylate収率 74.5%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Into a round-bottom flask, was placed a solution of tert-butyl 4-(4-cyanophenyl)-4-hydroxypiperidine-1-carboxylate (compound 1.2, 2 g, 6.61 mmol, 1.00 equiv) in pyridine (40 mL). POCl3 (10.16 g, 66.26 mmol, 10.02 equiv) was carefully added. The resulting mixture was stirred under nitrogen overnight at room temperature and then concentrated under vacuum. The residue was taken up in 20 mL of DCM, washed with 2×20 mL of sodium bicarbonate (aq), dried (Na2SO4), and concentrated under reduced pressure. The residue was purified using silica gel column chromatography with PE/EtOAc (100:1-30:1) as eluent to yield 1.4 g (74%) of the title compound as a white solid.

後処理

  1. customInto a round-bottom flask, was placed
  2. concentrationconcentrated under vacuum
  3. washwashed with 2×20 mL of sodium bicarbonate (aq)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified

出典と根拠

ORDレコード
ord-1577c826758d43b5879d3577b9cf0bc6
出典データセット
uspto-grants-2014_10
特許番号
US08871790B2

反応ノート

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