Trifluoroacetic anhydride → Tert-butyl 2-cyano-4,4-difluoropiperidine-1-carboxylate

HRID 526926

反応式

HRID 526926 の反応式
[C:1]([CH:4]1[CH2:9][C:8]([F:11])([F:10])[CH2:7][CH2:6][N:5]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)[NH2:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([CH:4]1[CH2:9][C:8]([F:11])([F:10])[CH2:7][CH2:6][N:5]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])#[N:2]

参加物

5

反応物 2

HCID 9845Trifluoroacetic anhydrideHCID 67286514Tert-butyl 2-carbamoyl-4,4-difluoropiperidine-1-carboxylate2 回

生成物 1

HCID 67284864Tert-butyl 2-cyano-4,4-difluoropiperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of tert-butyl 2-carbamoyl-4,4-difluoro-piperidine-1-carboxylate, 13g, (1.72 g, 6.51 mmol) in CH2Cl2 (50 mL) was added was N,N-triethylamine (2.03 mL, 14.61 mmol) followed by the dropwise addition of (2,2,2-trifluoroacetyl)-2,2,2-trifluoroacetate (1.02 mL, 7.32 mmol). After 15 minutes, the mixture was diluted with aqueous saturated NaHCO3 solution and the layers were separated. The organic phase was washed with water, dried over Na2SO4, filtered and evaporated to dryness. The crude residue was passed through a plug of silica gel and eluted with 10-30% EtOAc/hexanes to afford the desired product, 13h.

後処理

  1. customthe layers were separated
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. washeluted with 10-30% EtOAc/hexanes

出典と根拠

ORDレコード
ord-ceb5fbefd49c41c19d987aa9b349c68a
出典データセット
uspto-grants-2016_05
特許番号
US09345708B2

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