Riboflavin → 4-(Difluoromethyl)piperidine

HRID 930333Notes

Reaction equation

HRID 930333 reaction equation
[F:1][CH:2]([F:19])[CH:3]1[CH2:8][CH2:7][N:6](C(OCC2C=CC=CC=2)=O)[CH2:5][CH2:4]1.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C.[H][H]>[Pd].CCO>[F:1][CH:2]([F:19])[CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 493570RiboflavinHCID 86732159HCID 86732159, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 497591474-(Difluoromethyl)piperidineYield 15.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 250 flask charged with benzyl 4-(difluoromethyl)piperidine-1-carboxylate (1.16 g, 4.31 mmol), palladium, 10 wt. % (dry basis) on activated carbon, wet, degussa type e101 ne/w (0.563 g, 0.265 mmol) and EtOH (25 mL) was evacuated/backfilled with hydrogen (1 atm, 3×). After stirring overnight at room temperature, more palladium, 10 wt. % (dry basis) on activated carbon, wet, degussa type e101 ne/w (1.09 g) was added and the reaction was evacuated/backfilled with hydrogen (1 atm, 3×). After stirring overnight the reaction was filtered through a pad of Celite and the pad was washed with EtOH. Concentration of the filtrate in vacuo gave 4-(difluoromethyl)piperidine as a light-yellow oil (90 mg, 15% yield).

Workup

  1. dry with materialmore palladium, 10 wt. % (dry basis) on activated carbon
  2. additionwet, degussa type e101 ne/w (1.09 g) was added
  3. stirringAfter stirring overnight the reaction
  4. filtrationwas filtered through a pad of Celite
  5. washthe pad was washed with EtOH

Sources & evidence

ORD record
ord-a9c40d9dfb2140d388f53c82431d4fb2
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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