Allyl iodide → (4S)-3-{(2S)-2-[(5-methylindolyl)methyl]pent-4-enoyl}-4-phenyl-1,3-oxazolidin-2-one

HRID 498982Notes

Reaction equation

HRID 498982 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([CH2:21][CH2:22][C:23]([N:25]1[C@@H:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:28][O:27][C:26]1=[O:36])=[O:24])=[CH:15]2.[CH2:37](I)[CH:38]=[CH2:39]>C1COCC1>[CH3:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([CH2:21][C@H:22]([CH2:39][CH:38]=[CH2:37])[C:23]([N:25]1[C@@H:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:28][O:27][C:26]1=[O:36])=[O:24])=[CH:15]2

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68492500(4S)-3-[3-(5-methylindolyl)propanoyl]-4-phenyl-1,3-oxazolidin-2-one

Product 1

HCID 68493146(4S)-3-{(2S)-2-[(5-methylindolyl)methyl]pent-4-enoyl}-4-phenyl-1,3-oxazolidin-2-oneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of NaHMDS 1 M in THF (36.40 mL, 36.40 mmol) was added dropwise a solution of 8 (11.51 g, 33.04 mmol) in THF (180 mL) at −78° C. under argon. The solution was stirred at −78° C. (2 h), then allyl iodide (6.66 g, 39.65 mmol) in THF (70 mL) was added and the mixture was stirred for an additional 2 h at −78° C. The reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched by the addition of ice-cold saturated NH4Cl solution (200 mL), extracted with EtOAc, washed with brine and dried (Na2SO4). Evaporation provided a residue, which was purified by silica gel flash chromatography to provide 9 as colorless oil. (7.82 g, 61% yield). H NMR (d6-DMSO) δ 7.37-7.21 (m, 8H), 6.97 (dd, 1H, J=1.5 Hz & 8.5 Hz), 6.31 (dd, 1H, J=0.8 Hz & 3.1 Hz), 5.56 (m, 1H), 5.34 (dd, 1H, J=3.8 Hz & 8.5 Hz), 4.94-4.90 (m, 2H), 4.50 (t, 1H, J=8.7), 4.46-4.38 (m, 2H), 4.17 (m, 1H), 4.11 (dd, 1H, J=3.5 Hz & 8.8 Hz), 2.37 (s, 3H), 2.32 (m, 1H), 2.17 (m, 1H). FABMS (+Ve) m/z 388 [M+], 389 [MH+]. Anal. Calcd for C24H24N2O3 C, 74.21; H, 6.23; N, 7.21. Found C, 74.29; H, 6.22; N, 7.20.

Workup

  1. stirringthe mixture was stirred for an additional 2 h at −78° C
  2. temperatureThe reaction mixture was warmed to room temperature
  3. stirringstirred overnight
  4. customThe reaction was quenched by the addition of ice-cold saturated NH4Cl solution (200 mL)
  5. extractionextracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customEvaporation
  9. customprovided a residue, which
  10. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-91b7b41edcae4af297544150078a2c3d
Source dataset
uspto-grants-2010_08
Patent number
US07767645B2

Reaction notes

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