Hydrochloric Acid → HCID 15643567, compound

HRID 340977Notes

Reaction equation

HRID 340977 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-bdcbd65e619a403a97b9a6d271f341a5
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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