Hydrochloric Acid → HCID 15643567, compound

HRID 409839Notes

Reaction equation

HRID 409839 reaction equation
CC1(C)[N:6]2[C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH2:9][C@H:5]2[CH2:4][O:3]1.Cl.N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CO>[Si:20]([O:3][CH2:4][C@H:5]1[NH:6][C:7](=[O:12])[C:8]([CH3:10])([CH3:11])[CH2:9]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57415670HCID 57415670, compound

Product 1

HCID 15643567HCID 15643567, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-3,3,6,6-tetramethyl-dihydropyrrolo[1,2-c]oxazol-5(1H,3H,6H)-one in methanol (20 mL) was added HCl (4 N in 1,4-dioxane, 10 mL, 40 mmol). The reaction mixture was stirred at RT for 30 min, concentrated to dryness, and re-dissolved in DCM (50 mL). To the resulting solution were added imidazole (1.5 g, 22 mmol) and TBS-Cl (2.8 g, 18.6 mmol) respectively. The mixture was stirred at RT overnight and filtered. The filtrate was concentrated and the residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-5-((tert-butyldimethylsilyloxy)methyl)-3,3-dimethylpyrrolidin-2-one (3.1 g, 71.2%). LRMS (M+H+) m/z 258.3.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionre-dissolved in DCM (50 mL)
  3. stirringThe mixture was stirred at RT overnight
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified on silica gel column
  7. additiona mixture of EtOAc and hexanes

Sources & evidence

ORD record
ord-d5a38d2c695544b6af613f31723b6145
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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