Trimethylaluminum → HCID 86709517, compound

HRID 1848509Notes

Reaction equation

HRID 1848509 reaction equation
[CH3:1][C:2]1[C:6](=[O:7])[O:5][CH2:4][C:3]=1[N:8]1[CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[C:10]2([CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[C:9]1=[O:33].[CH3:34][Al](C)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:34][C:11]1[C:10]2([CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:24][CH2:25]2)[C:9](=[O:33])[N:8]([C:3]2[CH2:4][O:5][C:6](=[O:7])[C:2]=2[CH3:1])[CH:12]=1

Participants

5

Reactant 2

HCID 16682925TrimethylaluminumHCID 86709518HCID 86709518, compound

Product 1

HCID 86709517HCID 86709517, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-4-(((trifluoromethyl)sulfonyl)oxy)-2,8-diazaspiro[4.5]dec-3-ene-8-carboxylate (180 mg, 0.363 mmol) was dissolved in THF (3.6 mL), and Pd(Ph3P)4 (209 mg, 0.181 mmol) was added, followed by trimethylaluminum (3.6 mL, 7.25 mmol) at 0° C. This reaction was stirred at rt for 2 h before it was quenched with saturated aqueous NaHCO3 solution at 0° C. (highly exothermic). This mixture was diluted with EtOAc, dried over Mg2SO4 and concentrated under reduced pressure. The crude material was purified by column chromatography (0-10% MeOH/DCM) to afford the title compound. LC/MS: [(M+1)]+=363

Workup

  1. customwas quenched with saturated aqueous NaHCO3 solution at 0° C. (highly exothermic)
  2. additionThis mixture was diluted with EtOAc
  3. dry with materialdried over Mg2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by column chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-a369984abc8b4db798bc6153ef6744f2
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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