Benzyl Bromide → HCID 22928671, compound

HRID 1453914Notes

Reaction equation

HRID 1453914 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[O:11]=[C:12]1[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][N:13]1[C:20]([O-:22])=[O:21].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH2:23]([CH:16]1[CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][N:13]([C:20]([O:22][C:15]([CH3:17])([CH3:16])[CH3:14])=[O:21])[C:12]1=[O:11])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 25517Ammonium ChlorideHCID 22928679HCID 22928679, compoundHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 22928671HCID 22928671, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A 1.0 M tetrahydrofuran solution of lithium hexamethyldisilazane (6.2 ml, 6.2 mmol) was gradually added to a solution of tert-butyl. 2-oxo-4-propyl-1-pyrrolidinecarboxylate (1.35 g, 5.94 mmol) in tetrahydrofuran (20 ml) at −70° C. and the mixture was stirred for 15 minutes. Benzyl bromide was added to the reaction mixture and the temperature of the mixture was gradually raised to 0° C. and it was stirred for 3 hours. Saturated aqueous ammonium chloride solution was added to the reaction mixture and extraction was performed with ethyl acetate. After washing the organic layer with brine and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1.22 g) as a light yellow oil. 1H-NMR (CDCl3) δ(ppm) 0.80 (3H, t, J=7.2 Hz), 1.10-1.40 (4H, m), 1.52 (9H, s), 1.87-1.95 (1H, m), 2.44-2.52 (1H, m), 2.90 (1H, dd, J=14.4 Hz, 7.2 Hz), 3.10 (1H, dd, J=14.4 Hz, 5.2 Hz), 3.15 (1H, dd, J=10.8 Hz, 8.0 Hz), 3.71 (1H, dd, J=10.8 Hz, 8.0 Hz), 7.15-7.33 (5H, m)

Workup

  1. washAfter washing the organic layer with brine
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-8e234918de534df5b61985ef5449c00c
Source dataset
uspto-grants-2009_01
Patent number
US07476688B2

Reaction notes

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