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

HRID 1901725Notes

Reaction equation

HRID 1901725 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-dca3edc3897d4615b27d111de924c071
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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