Imidazole → HCID 131731720, compound

HRID 1632092Notes

Reaction equation

HRID 1632092 reaction equation
OC[C@H]1N[C:6](=O)[CH2:5][CH2:4]1.[CH3:9][N:10]([CH:12]=[O:13])C.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])(C)C.N1[CH:26]=[CH:25]N=C1.[OH2:27]>>[C:17]([SiH2:14][O:27][C:5]([CH3:4])([CH3:6])[C@H:9]1[NH:10][C:12](=[O:13])[CH2:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 131731720HCID 131731720, compoundYield 96%

Procedure

A solution of (S)-5-hydroxymethyl-pyrrolidin-2-one (1.0 g, 8.69 mmol), DMF (10 mL), t-butyldimethylsilyl chloride (1.57 g, 10.42 mmol), and imidazole (0.89 g, 13.03 mmol) was stirred at ambient temperature for 4 hours after which time 4 mL of water were added. The layers were separated and the aqueous was extracted with dichloromethane (10 mL). The combined organics were washed with water (15 mL) and brine (15 mL), dried with sodium sulfate, filtered and concentrated to afford 1.91 g of I-188 as a colorless oil in 96% yield.

Workup

  1. additionwere added
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with dichloromethane (10 mL)
  4. washThe combined organics were washed with water (15 mL) and brine (15 mL)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford 1.91 g of I-188 as a colorless oil in 96% yield

Sources & evidence

ORD record
ord-c42fabc2aaee45d1be24ab9479b27a2a
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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