Imidazole → (2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate

HRID 1600911Notes

Reaction equation

HRID 1600911 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C@@H:9]([OH:12])[CH2:10][OH:11])[CH:2]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.N1C=CN=C1.[Si:29](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]>N1C=CC=CC=1.ClCCl.CN(C)C=O>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O:11][CH2:10][C@H:9]([O:12][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 73974-Toluenesulfonyl chlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 12972952(2R)-4-(3-pyridyl)-1,2-butanediol

Product 1

HCID 54162583(2R)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonateYield 66.8%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Prepared according to the method described in Example 26d) from (2R)-4-(3-pyridyl)-1,2-butanediol (5 g) and para-toluenesulfonyl chloride (8.60 g) in pyridine (30 ml) and dichloromethane (30 ml). The resulting adduct was treated with imidazole (3.4 g) and tert-butyldimethylsilyl chloride (5.25 g) in dimethylformamide (20 ml) to give the sub-title compound as an oil (8.7 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-cec2a2b69eb54f7faf7f4b7e42b89fe9
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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