Methyl iodide → HCID 86725346, compound

HRID 925239Notes

Reaction equation

HRID 925239 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:27][CH2:26][C:15]2[C:16]3[CH:17]([OH:25])[C:18]([F:24])([F:23])[CH2:19][C:20]=3[CH:21]=[CH:22][C:14]=2[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[CH3:30]I>C1COCC1.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:27][CH2:26][C:15]2[C:16]3[CH:17]([O:25][CH3:30])[C:18]([F:23])([F:24])[CH2:19][C:20]=3[CH:21]=[CH:22][C:14]=2[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 4311764Sodium borohydrideHCID 86725345HCID 86725345, compound

Product 1

HCID 86725346HCID 86725346, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product from step (c) (0.13 g, 0.35 mmol) dissolved in THF (2 ml) at 0° C. was added NaH (0.046, 0.86 mmol). The reaction mixture was allowed to stir for 10 minutes followed by the addition of methyl iodide (0.053 mL, 0.86 mmol). The reaction mixture was stirred at RT for 24 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined ethyl acetate extracts were washed with brine, dried (Na2SO4), and solvent evaporated in vacuo to give the sub-titled compound as a yellow oil (0.10 g). MS: ESI (positive): 388 (M+H).

Workup

  1. stirringThe reaction mixture was stirred at RT for 24 hours
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined ethyl acetate extracts were washed with brine
  4. dry with materialdried (Na2SO4), and solvent
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a385eca632eb45578c89e8e2cd70f76f
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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