Allyl bromide → HCID 54134730, compound

HRID 617354Notes

Reaction equation

HRID 617354 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([CH2:7][O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[NH:3]1.[H-].[Na+].[CH2:17](Br)[CH:18]=[CH2:19]>C1COCC1>[CH2:19]([N:3]1[C@H:4]([CH2:7][O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:6][C:2]1=[O:1])[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 54043018HCID 54043018, compound2×

Product 1

HCID 54134730HCID 54134730, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((2-oxo-5-(S)-pyrrolidinyl)methoxy)pyridine, from Example 22a (450 mg, 2.34 mmol), in 10 mL of anhydrous THF at 0° C. was added NaH (80% dispersion, 186 mg, 2.68 mmol) was added, and the reaction mixture was stirred for 20 minutes at this temperature. The reaction was then warmed to room temperature, and allyl bromide (425 mg, 3.51 mmol) was added via syringe. After starting material was consumed, water was added to quench the reaction. The desired compound was extracted from the aqueous phase with ethyl acetate and chloroform. The organic layer was dried over MgSO4, then taken to dryness. The residue was purified by silica gel flash chromatography (5% MeOH/CHCl3) to give 450 mg of the title compound. MS (DCI/NH3) m/e: 233 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 8.37-8.26 (m, 2H), 7.38-7.29 (m, 2H), 5.83-5.69 (m, 1H), 5.26-5.13 (m, 2H), 4.35-4.24 (m, 1H), 4.16-3.96 (m, 3H), 3.77-3.67 (m, 1H), 2.68-2.54 (m, 1H), 2.50-2.38 (m, 1H), 2.36-2.20 (m, 1H), 2.09-1.96 (m, 1H),

Workup

  1. customat 0° C.
  2. additionwas added
  3. customwas consumed
  4. additionwater was added
  5. customto quench
  6. customthe reaction
  7. extractionThe desired compound was extracted from the aqueous phase with ethyl acetate and chloroform
  8. dry with materialThe organic layer was dried over MgSO4
  9. customThe residue was purified by silica gel flash chromatography (5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-5d46b3da04224ec99bd5cfa677c26e60
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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