Imidazole → Methyl 2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy]ethyl)benzoate

HRID 916069Notes

Reaction equation

HRID 916069 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([C@@H:19]([OH:22])[CH2:20][Br:21])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>CN(C1C=CN=CC=1)C.CN(C)C=O>[CH3:14][O:13][C:11](=[O:12])[C:10]1[CH:15]=[C:16]([C@@H:19]([O:22][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:20][Br:21])[CH:17]=[CH:18][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11003029(R)-Methyl 2-(benzyloxy)-5-(2-bromo-1-hydroxyethyl)benzoate

Product 1

HCID 57438683Methyl 2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy]ethyl)benzoateYield 97.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]benzoate (71.0 g, 195 mmol), imidazole (18.5 g, 272 mmol), tert-butyldimethylsilyl chloride (32.2 g, 214 mmol) and 4-(N,N-dimethylamino)pyridine (440 mg, 3.60 mmol) in N,N-dimethylformamide (270 ml) was left to stir at room temperature under a nitrogen atmosphere for a period of 24 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (500 ml) and water (500 ml). The organic phase was separated and washed with 2N aqueous hydrochloric acid (2×500 ml), saturated aqueous sodium bicarbonate (2×500 ml), brine (500 ml), dried (magnesium sulfate) and the solvent removed in vacuo to give the title compound as a colourless oil (91.0 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (500 ml) and water (500 ml)
  3. customThe organic phase was separated
  4. washwashed with 2N aqueous hydrochloric acid (2×500 ml), saturated aqueous sodium bicarbonate (2×500 ml), brine (500 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d60dbd3c89c448f5a2923534265b8fe6
Source dataset
uspto-grants-2007_09
Patent number
US07268147B2

Reaction notes

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