Imidazole → (2r)-1-(4-Bromophenoxy)-4-(3-pyridyl)-2-(tert-butyldimethylsilyloxy)butane

HRID 1386018Notes

Reaction equation

HRID 1386018 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[Br:14][C:15]1[CH:32]=[CH:31][C:18]([O:19][CH2:20][C@H:21]([OH:30])[CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:17][CH:16]=1>ClCCl>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][C@H:21]([O:30][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 53756856(2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol

Product 1

HCID 54062431(2r)-1-(4-Bromophenoxy)-4-(3-pyridyl)-2-(tert-butyldimethylsilyloxy)butaneYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyldimethylsilylchloride (3.75 g) and imidazole (1.69 g) were added to a solution of (2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol (4 g, Example 21a)) in dichloromethane. The mixture was stirred for 16 hours at room temperature. The white precipitate was collected by filtration and the filtrate concentrated under reduced pressure to give the sub-title compound as an oil (5.4 g)

Workup

  1. filtrationThe white precipitate was collected by filtration
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-70552c409e884970afd47d504e5b74a3
Source dataset
uspto-grants-2001_07
Patent number
US06265409B1

Reaction notes

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