Sodium hydride → N-Cbz-4-[4-(1,4-Dioxapent-1-yl)phenyl]butylamine
Reaction equation
[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]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
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).
Workup
- stirringthe mixture was stirred at room temperature overnight
- customThe solvent was removed under reduced pressure
- customthe material was purified by column chromatography (silica gel, 10:1 methylene chloride/ethyl acetate)
Sources & evidence
- ORD record
- ord-02db019f217442d79c530f1d2f4a1b1d
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198286B2
Reaction notes
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