Sodium hydride → N-Cbz-4-[4-(1,4-Dioxapent-1-yl)phenyl]butylamine

HRID 25130

反応式

HRID 25130 の反応式
[C:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[H-].[Na+].[CH3:25][O:26][CH2:27][CH2:28]Br>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:28][CH2:27][O:26][CH3:25])=[CH:18][CH:17]=1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 11637991N-Cbz4-(4-hydroxyphenyl)butylamine

生成物 1

HCID 22566171N-Cbz-4-[4-(1,4-Dioxapent-1-yl)phenyl]butylamine収率 66.7%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a vigorously stirred solution of 29 (4 g, 0.013 mol) in anhydrous THF (150 mL) under nitrogen at 0° C. was added sodium hydride (60% dispersion in mineral oil, 0.64 g, 0.016 mol). The mixture was stirred for 15 min then tetrabutylammonium iodide (0.5 g, 0.0013 mol) and 2-bromoethyl methyl ether (2.04 g, 0.015 mol) were added and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the material was purified by column chromatography (silica gel, 10:1 methylene chloride/ethyl acetate) to provide 64 (3.1 g, 64%). 1H NMR (300 MHz, CDCl3) δ 1.60 (m, 4H), 2.59 (m, 2H), 3.23 (m, 2H), 3.45 (s, 3H), 3.77 (m, 2H), 4.10 (m, 2H), 5.13 (s, 2H), 6.88 (d, 2H), 7.08 (d, 2H), 7.47 (s, 5H).

後処理

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe material was purified by column chromatography (silica gel, 10:1 methylene chloride/ethyl acetate)

出典と根拠

ORDレコード
ord-4a2186cd1db345cfbc7dd8289da03907
出典データセット
uspto-grants-2005_02
特許番号
US06858615B2

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