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

HRID 25130

반응식

HRID 25130 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4a2186cd1db345cfbc7dd8289da03907
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858615B2

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