2,3-Epoxypropyl 4'-methoxyphenyl ether → 1-(4-Methoxyphenoxymethyl)-2-(2-t-butyldimethylsilyloxy-1-methylethylamino)ethanol

HRID 2294339Notes

Reaction equation

HRID 2294339 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([NH2:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:13][O:14][C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][CH:21]2[CH2:23][O:22]2)=[CH:17][CH:16]=1>C(O)C>[CH3:13][O:14][C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][CH:21]([OH:22])[CH2:23][NH:12][CH:10]([CH3:11])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 166462,3-Epoxypropyl 4'-methoxyphenyl etherHCID 21474737(S)-2-Amino-tert-butyldimethylsilyloxypropane

Product 1

HCID 214747001-(4-Methoxyphenoxymethyl)-2-(2-t-butyldimethylsilyloxy-1-methylethylamino)ethanolYield 58.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A procedure similar to that described in Preparation 10 was repeated, except that 3.22 g of 2-t-butyldimethylsilyloxy-1-methylethylamine, 3.00 g of 4-methoxyphenoxymethyloxirane and 30 ml of ethanol were used, to give 3.58 g of the title compound having an Rf value of 0.15 (on silica gel thin layer chromatography, using ethyl acetate as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 10

Sources & evidence

ORD record
ord-1dcd9b56b0d54986acc5f8d82282a1ce
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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