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Triethylamine → 4-[(r)-2-(4-Benzyl-phenoxymethyl)-pyrrolidin-1-ylmethyl]-pyridine

HRID 749932
ノート
印刷プレビュー

反応式

HRID 749932 の反応式
[CH2:1]([C:8]1[CH:20]=[CH:19][C:11]([O:12][CH2:13][C@H:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[N:22]1[CH:27]=[CH:26][C:25]([CH2:28]Cl)=[CH:24][CH:23]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([C:8]1[CH:20]=[CH:19][C:11]([O:12][CH2:13][C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH2:28][C:25]2[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=2)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 745704-(Chloromethyl)pyridinium chlorideHCID 16222640(2r)-2-[(4-Benzylphenoxy)methyl]pyrrolidine

生成物 1

HCID 162226434-[(r)-2-(4-Benzyl-phenoxymethyl)-pyrrolidin-1-ylmethyl]-pyridine収率 45%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of Example 1 (0.25 g, 0.82 mmol) in dichloromethane (2 mL) was added 4-picolyl chloride hydrochloride (0.13 g, 0.79 mmol) and triethylamine (0.29 mL, 2.08 mmol). The resulting mixture was stirred at ambient temperature overnight. The crude product was extracted into dichloromethane and washed with water followed by brine. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.11 g, 45%); 1NMR (400 MHz, CDCl3); δ 1.70-1.81 (m, 3H), 2.03 (m, 1H), 2.27 (m, 1H), 2.94-3.03 (m, 2H), 3.49 (d, J=14.4 Hz, 1H), 3.86 (m, 1H), 3.92 (s, 2H), 3.94 (m, 1H), 4.19 (d, J=14.4 Hz, 1H), 6.79 (d, J=8.8 Hz, 2H), 7.08 (d, J=8.8 Hz, 2H), 7.15-7.20 (m, 3H), 7.26-7.29 (m, 4H), 8.51 (m, 2H); MS (m/z) 359.5 (M+1); LC (99.7%); HPLC (91.6%)

後処理

  1. extractionThe crude product was extracted into dichloromethane
  2. washwashed with water
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-9009347b11e1498990a57a342755e5e7
出典データセット
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07402684B2

反応ノート

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