Imidazole → HCID 67148860, compound

HRID 2428165Notes

Reaction equation

HRID 2428165 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]2)=[CH:4][CH:3]=1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1.[NH4+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C@H:10]([O:13][Si:18]([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 67148437HCID 67148437, compound

Product 1

HCID 67148860HCID 67148860, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-1-(4-Bromo-phenyl)-pyrrolidin-3-ol (14.0 g, 57.7 mmol) was dissolved in DMF (100 mL), and TBDMS-Cl (10.4 g, 69.2 mmol) and imidazole (9.81 g, 144 mmol) were added. The mixture was stirred at rt overnight. Aq. sat. NH4Cl (100 mL) was added, and the mixture was extracted with heptane (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:15→1:4) yielded the title compound (17.3 g, 84%).

Workup

  1. extractionthe mixture was extracted with heptane (2×)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (EtOAc/heptane 1:15→1:4)

Sources & evidence

ORD record
ord-1d668481f4954cda9ddee08a0f1bb970
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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