Methyl iodide → HCID 71140771, compound

HRID 1468856Notes

Reaction equation

HRID 1468856 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][O:7][C@H:8]([C@@H:11]2[CH2:13][C@@H:12]2[CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:25]=[CH:24][C:23]([CH2:26][CH3:27])=[CH:22][N:21]=3)[CH2:16][CH2:15]2)[CH2:9][OH:10])=[CH:4][CH:3]=1.[CH3:30][Si]([N-][Si](C)(C)C)(C)C.[Na+].CI>C1COCC1>[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][O:7][C@H:8]([C@@H:11]2[CH2:13][C@@H:12]2[CH:14]2[CH2:15][CH2:16][N:17]([C:20]3[N:21]=[CH:22][C:23]([CH2:26][CH3:27])=[CH:24][N:25]=3)[CH2:18][CH2:19]2)[CH2:9][O:10][CH3:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 71140750HCID 71140750, compound

Product 1

HCID 71140771HCID 71140771, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.), stirred solution of the product of step F (0.70 g, 1.52 mmol) in THF (6 mL) was added NaHMDS (1.6 mL of 1.0 M solution in THF, 1.60 mmol) dropwise. Upon stirring at −78° C. for 15 min the mixture was warmed to 0° C. when MeI (0.43 g, 3.04 mmol) was added. The cold bath was removed and the mixture was stirred at RT for 3 h before being quenched with a saturated aqueous solution of NH4Cl. The solution was extracted with Et2O (×3). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated under vacuum to leave a residue which was purified by column chromatography on silica (elution with 5:1 hexane:ethyl acetate) to yield the title compound. MS (ESI) m/z 474/476 [M+H]+.

Workup

  1. additionwas added
  2. customThe cold bath was removed
  3. stirringthe mixture was stirred at RT for 3 h
  4. custombefore being quenched with a saturated aqueous solution of NH4Cl
  5. extractionThe solution was extracted with Et2O (×3)
  6. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto leave a residue which
  10. customwas purified by column chromatography on silica (elution with 5:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-3edb17eaab1043f089a2f1234b4f0697
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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