Selectfluor → Benzyl 3-fluoro-4-oxopiperidine-1-carboxylate

HRID 876481Notes

Reaction equation

HRID 876481 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.C[Si](C)(C)[O:24][C:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[CH2:27][CH:26]=1>CC#N>[F:21][CH:30]1[C:25](=[O:24])[CH2:26][CH2:27][N:28]([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[CH2:29]1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 57502431Benzyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 42609253Benzyl 3-fluoro-4-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Selectfluor® (181.2 g, 511.4 mmol) was added portion-wise (about 25 g portions) to a ice cold solution of benzyl 4-(trimethylsilyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (142 g, 465 mmol) in CH3CN (2 L) over approximately 30 minutes. The ice bath was removed and the mixture was allowed to stand for 12 hours. The mixture was concentrated to a slurry, diluted with EtOAc and brine and the layers were separated. The brine phase was extracted once with EtOAc, and the combined organic phases were washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo to provide the desired product as a dark thick oil (112 g).

Workup

  1. customThe ice bath was removed
  2. concentrationThe mixture was concentrated to a slurry
  3. additiondiluted with EtOAc and brine
  4. customthe layers were separated
  5. extractionThe brine phase was extracted once with EtOAc
  6. washthe combined organic phases were washed with saturated NaHCO3 and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f72f4b9f00d5452ab751e7ddfa21229a
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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