Myosmine → 3-(Pyrrolidin-2-yl)pyridine

HRID 384842

反応式

HRID 384842 の反応式
[CH:1]1[CH:6]=[N:5][CH:4]=[C:3]([C:7]2[CH2:11][CH2:10][CH2:9][N:8]=2)[CH:2]=1>CO.[Pd]>[CH:1]1[CH:6]=[N:5][CH:4]=[C:3]([CH:7]2[NH:8][CH2:9][CH2:10][CH2:11]2)[CH:2]=1

参加物

4

反応物 1

HCID 442649Myosmine

生成物 1

HCID 4123-(Pyrrolidin-2-yl)pyridine収率 84.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

Myosmine (32 g, 0.219 mol) was dissolved in 150 ml of methanol and hydrogenated at atmospheric pressure with 1.3 g of 10% palladium on carbon as catalyst. After 5 hours the mixture was filtered and the filtrate was concentrated to get a brown solid (32 g, 94.9% purity by GC). It was further purified by vacuum distillation at 0.1 mm Hg to get pure nornicotine (27.46 g, 84.7% yield, 97.5% purity by GC). 1H NMR (CDCl3): δ 1.66-2.72 (2H, m), 3.0 (2H, m), 4.13 (1H, t), 7.24 (1H, m), 7.69 (1H, dt), 8.46 (1H, dd), and 8.59 (1H, d). 13C-NMR (CDCl3): δ 148.4, 148.1, 140.16, 134.1, 123.3, 60.0, 46.8, 34.2, and 25.4. IR: 3291, 2960, 1641, 1578 Cm−1.

後処理

  1. filtrationAfter 5 hours the mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto get a brown solid (32 g, 94.9% purity by GC)
  4. distillationIt was further purified by vacuum distillation at 0.1 mm Hg

出典と根拠

ORDレコード
ord-4b86f3b21fca4c0f8cd745f262d0f737
出典データセット
uspto-grants-2013_02
特許番号
US08367837B2

関連ノート

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