Imidazole → HCID 57260263, compound

HRID 339731Notes

Reaction equation

HRID 339731 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CN=C1.[CH3:21][C:22]([Si:25](Cl)([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C=O)C>[Si:25]([O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:22]([CH3:24])([CH3:23])[CH3:21])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 562256Benzyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 57260263HCID 57260263, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl 3-hydroxypropylcarbamate (15 g, 72 mmol) was treated with imidazole (10 g, 146.9 mmol) and TBSCl (12 g, 79.6 mmol) in DMF (10 ml) at 0° C. After warming up the reaction mixture to room temperature, it was stirred for 30 minutes. The resulting solution was quenched with water (50 ml), and then extracted with diethyl ether (50 ml×2) twice. After evaporation of volatile material under reduced pressure, the residue was purified with silica gel column chromatography (EtOAc:Hx=1:10) to afford title compound (23 g, 98%) as colorless oil.

Workup

  1. customThe resulting solution was quenched with water (50 ml)
  2. extractionextracted with diethyl ether (50 ml×2) twice
  3. customAfter evaporation of volatile material under reduced pressure
  4. customthe residue was purified with silica gel column chromatography (EtOAc:Hx=1:10)

Sources & evidence

ORD record
ord-df6f156413d74ef5af98b71d72c4e7c0
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Reaction notes

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