Tert-butyl 2-cyano-4,4-difluoropiperidine-1-carboxylate → Tert-butyl 2-(aminomethyl)-4,4-difluoropiperidine-1-carboxylate

HRID 74903Notes

Reaction equation

HRID 74903 reaction equation
[C:1]([CH:3]1[CH2:8][C:7]([F:10])([F:9])[CH2:6][CH2:5][N:4]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])#[N:2]>[Ni].CO>[NH2:2][CH2:1][CH:3]1[CH2:8][C:7]([F:10])([F:9])[CH2:6][CH2:5][N:4]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

4

Reactant 1

HCID 67284864Tert-butyl 2-cyano-4,4-difluoropiperidine-1-carboxylate2×

Product 1

HCID 67286116Tert-butyl 2-(aminomethyl)-4,4-difluoropiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

Raney nickel (0.36 mL, 5.40 mmol) was washed with MeOH (2×) and charged into a parr shaker. A solution of tert-butyl 2-cyano-4,4-difluoro-piperidine-1-carboxylate, 13h, (1.33 g, 5.40 mmol) in methanol (50 mL). The reaction mixture was subject to hydrogenation conditions overnight on the parr shaker (46PSI). The mixture was filtered through celite and washed thoroughly with CH2Cl2. All volatiles were removed at reduced pressure and the crude material was used without further purification.

Workup

  1. additioncharged into a parr shaker
  2. customwas subject to hydrogenation conditions overnight on the parr shaker (46PSI)
  3. filtrationThe mixture was filtered through celite
  4. washwashed thoroughly with CH2Cl2
  5. customAll volatiles were removed at reduced pressure
  6. customthe crude material was used without further purification

Sources & evidence

ORD record
ord-593840bea670413cbb3d58b918e1f8d6
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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