Methyl iodide → HCID 71186642, compound

HRID 712789Notes

Reaction equation

HRID 712789 reaction equation
[CH2:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]([C:16]([O:18][CH3:19])=[O:17])[CH2:4]2)[CH2:2]1.[Li+].[CH3:21]C([N-]C(C)C)C.C1COCC1.CCCCCCC.IC.[NH4+].[Cl-]>C1COCC1>[CH3:21][C:5]1([C:16]([O:18][CH3:19])=[O:17])[N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:7][CH2:8][C:3]2([CH2:2][CH2:1]2)[CH2:4]1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 21263495Tetrahydrofuran heptaneHCID 71187452HCID 71187452, compound

Product 1

HCID 71186642HCID 71186642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

6-tert-butyl 5-methyl 6-azaspiro[2.5]octane-5,6-dicarboxylate (D4) (420 mg, 1.56 mmol) was dissolved in THF (25 ml) and the solution was cooled at −78° C. prior addition of LDA 2M sol in THF/heptane (1.16 ml, 2.34 mmol). The red solution was left stirring at −78° C. for 40 min before adding iodomethane (0.146 ml, 2.34 mmol). The reaction was allowed to warm to RT and left stirring for 3 hrs. The resulting yellow-orange solution was treated with NH4Cl sat. sol. (5 ml) and extracted with Et2O (3×50 ml). Collected organic phases were washed with NaCl sat. sol. and dried over Na2SO4. Collected organics after solvent evaporation, afforded a residue which was purified by Biotage SNAP-Si (25 g) eluting with DCM. Collected fractions after solvent evaporation afforded the title compound (D5) (320 mg)

Workup

  1. waitThe red solution was left
  2. temperatureto warm to RT
  3. waitleft
  4. stirringstirring for 3 hrs
  5. extractionextracted with Et2O (3×50 ml)
  6. washCollected organic phases were washed with NaCl sat. sol.
  7. dry with materialdried over Na2SO4
  8. customCollected organics after solvent evaporation
  9. customafforded a residue which
  10. customwas purified by Biotage SNAP-Si (25 g)
  11. washeluting with DCM
  12. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-d298a2f71e3c44c5b21af1363eed9d82
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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