Imidazole → HCID 131729338, compound

HRID 340940Notes

Reaction equation

HRID 340940 reaction equation
OCC1N[C:6](=[O:8])[CH2:5]C1.N1[CH:13]=[CH:12]N=C1.[CH3:14][C:15]([Si:18](Cl)(C)C)([CH3:17])[CH3:16].[CH3:22]COC(C)=O.[CH3:28][N:29]([CH:31]=[O:32])C>[Cl-].[Na+].O>[C:15]([SiH2:18][O:8][C:6]([CH3:5])([CH3:22])[CH:28]1[NH:29][C:31](=[O:32])[CH2:13][CH2:12]1)([CH3:17])([CH3:16])[CH3:14]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 5583595-(Hydroxymethyl)pyrrolidin-2-one

Product 1

HCID 131729338HCID 131729338, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-hydroxymethyl-pyrrolidin-2-one (20 g, 0.174 mol) in DMF (100 mL) was added imidazole (17.7 g, 0.260 mol) followed by TBDMSCl (27.5 g, 0.182 mol). After 2.5 h, LCMS analysis revealed reaction was complete. EtOAc (600 mL) and brine (300 mL) were added to the reaction solution. The aqueous layer was further extracted with EtOAc (2×350 mL). The combined organic layers were washed with brine, dried, and concentrated to give 5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-2-one (39.5 g) as a light yellow oil which was used in the next step without further purification. LRMS (M+H+) m/z 230.1.

Workup

  1. customreaction
  2. extractionThe aqueous layer was further extracted with EtOAc (2×350 mL)
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8aa514ae2784410d8d1333e6c8a74090
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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