2-((1,1-Dimethylethoxy)methyl)oxirane → N-(2-Hydroxy-3-t-butoxypropyl)-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine

HRID 376915

Reaction equation

HRID 376915 reaction equation
[C:1]([O:5][CH2:6][CH:7]1[O:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH3:10][C:11]([NH2:22])([CH3:21])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1>>[OH:9][CH:7]([CH2:6][O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:8][NH:22][C:11]([CH3:21])([CH3:10])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 243142-((1,1-Dimethylethoxy)methyl)oxiraneHCID 918922-(4-Methoxyphenyl)-1,1-dimethylethylamine

Product 1

HCID 22640942N-(2-Hydroxy-3-t-butoxypropyl)-1,1-dimethyl-2-(4-methoxyphenyl)ethylamineYield 34.3%

Procedure

Using the method of Example 15, supra, t-butylglycidyl ether (142 mg, 1.0 mmol) and 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (197 mg, 1.1 mmol) were used to prepare 106 mg of the title compound as a clear, colorless oil: GC/EI-MS, m/z (rel. int.) 310 (M+1. 0.3), 294 (0.5), 222 (1.8), 188 (67.9), 163 (14.6), 132 (100), 121 (19.1); 1H-NMR (CDCl3) δ 7.09 (2H, d, J=8.6), 6.82 (2H, d, J=8.6), 3.78 (3H, s), 3.68 (1H, m), 3.37 (2H, m), 2.27 (1H, dd, J=11.5 and 4.2), 2.63 (3H, m), 1.19 (9H, s), 1.05 (3H, s), 1.03 (3H, s); 13C-NMR (CDCl3) δ 156.0, 131.3, 130.3, 113.3, 72.9, 69.7, 64.5, 55.1, 52.9, 46.6, 44.7, 27.4, 26.9, 26.8.

Sources & evidence

ORD record
ord-da2915572d714fae8880fc6baf42ee22
Source dataset
uspto-grants-2000_02
Patent number
US06022894

Linked notes

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