Imidazole → HCID 58072157, compound

HRID 1260185Notes

Reaction equation

HRID 1260185 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.N1C=CN=C1.[Si:18](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[Si:18]([O:1][CH:2]1[CH2:3][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5]1)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 58072157HCID 58072157, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20.0 g (115 mmol) of tert-butyl 3-hydroxyazetidine-1-carboxylate and 9.43 g (139 mmol) of imidazole were initially charged in 200 ml of anhydrous DMF, and 34.91 g (127 mmol) of tert-butyl(diphenyl)silyl chloride were added at RT. After the reaction mixture had been stirred at RT for 18 h, it was poured into 3.2 liters of water and then extracted three times with approx. 1 liter each time of diethyl ether. The combined organic extracts were washed successively with saturated sodium hydrogencarbonate solution, water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate, the mixture was filtered and the solvent was removed on a rotary evaporator. The remaining residue was stirred with 100 ml of pentane for a few minutes. Subsequently, the solid was filtered off with suction and dried under high vacuum. 29.18 g (61% of theory) of the title compound were obtained.

Workup

  1. extractionextracted three times with approx. 1 liter each time of diethyl ether
  2. washThe combined organic extracts were washed successively with saturated sodium hydrogencarbonate solution, water and saturated sodium chloride solution
  3. dry with materialAfter drying over anhydrous magnesium sulphate
  4. filtrationthe mixture was filtered
  5. customthe solvent was removed on a rotary evaporator
  6. stirringThe remaining residue was stirred with 100 ml of pentane for a few minutes
  7. filtrationSubsequently, the solid was filtered off with suction
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-bdeff929fcb1434bbcec89f22d1f0a92
Source dataset
uspto-grants-2013_06
Patent number
US08470811B2

Reaction notes

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