Sodium borohydride → N-[2-(4-(2-Hydroxyethoxy)phenyl)-1-methylethyl]-N-(2-hydroxy-ethyl)-2-hydroxy-2-(2-chloro-thiazol-4-yl)ethanamine

HRID 1451467Notes

Reaction equation

HRID 1451467 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:10])[CH2:8]Br)[N:6]=1.[OH:11][CH2:12][CH2:13][NH:14][CH:15]([CH3:29])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25](OC)=[O:26])=[CH:19][CH:18]=1.[BH4-].[Na+]>CO>[OH:26][CH2:25][CH2:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH:15]([N:14]([CH2:13][CH2:12][OH:11])[CH2:8][CH:7]([OH:10])[C:5]2[N:6]=[C:2]([Cl:1])[S:3][CH:4]=2)[CH3:29])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 143477622-Chloro-4-bromoacetyl-thiazoleHCID 14347764HCID 14347764, compound

Product 1

HCID 19380190N-[2-(4-(2-Hydroxyethoxy)phenyl)-1-methylethyl]-N-(2-hydroxy-ethyl)-2-hydroxy-2-(2-chloro-thiazol-4-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared by analogy to Example 30 by reaction of 2-chloro-4-bromoacetyl-thiazole with N-(2-hydroxyethyl)-2-(4-carbomethoxymethoxyphenyl)-1-methylethylamine followed by reduction in methanol with sodium borohydride at room temperature. The crude product is purified on a silica gel column using chloroform/ ethyl acetate/ methanol=10:9:1 as eluant.

Workup

  1. customThe crude product is purified on a silica gel column

Sources & evidence

ORD record
ord-5eb6adca7b544ef6837c2437dd70f243
Source dataset
uspto-grants-1997_02
Patent number
US05604225

Reaction notes

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