Imidazole → (3R,4S)-3-[4-(4-Bromo-phenoxy)-3-(tert-butyl-dimethyl-silanyloxy)-pentyl]-pyridine

HRID 1856694Notes

Reaction equation

HRID 1856694 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C@H:7]([C@H:9]([OH:18])[CH2:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH3:8])=[CH:4][CH:3]=1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>ClCCl>[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C@@H:7]([CH3:8])[C@H:9]([O:18][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57304612(2S,3R)-2-(4-bromophenoxy)-5-pyridin-3-ylpentan-3-ol

Product 1

HCID 57150561(3R,4S)-3-[4-(4-Bromo-phenoxy)-3-(tert-butyl-dimethyl-silanyloxy)-pentyl]-pyridineYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,3R)-2-(4-bromophenoxy)-5-pyridin-3-ylpentan-3-ol (2.01 g, Example 15d)) in dry dichloromethane (50 ml) was added tert-butyldimethylsilyl chloride (1.81 g) and imidazole (0.814 g) and the resulting solution stirred for 24 hours, concentrated and the residue purified by column chromatography on silica gel eluting with dichloromethane:diethyl ether (1:1) to afford the sub-title compound as an oil (2.52 g).

Workup

  1. concentrationconcentrated
  2. customthe residue purified by column chromatography on silica gel eluting with dichloromethane:diethyl ether (1:1)

Sources & evidence

ORD record
ord-216f727cf4954bd7b10515f91cd5589d
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

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