Acetic Acid → HCID 59334005, compound

HRID 331079

Reaction equation

HRID 331079 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[F:12][C:13]([F:18])([F:17])[CH2:14][CH:15]=O.CC(O)=O.C([BH3-])#N.[Na+]>C1COCC1.CO>[F:12][C:13]([F:18])([F:17])[CH2:14][CH2:15][N:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 680283,3,3-TrifluoropropanalHCID 70770Ethyl 4-piperidinecarboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 59334005HCID 59334005, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl isonipecotate (3.00 g, 19.1 mmol) in THF (20 mL) and MeOH (20 mL) was added 3,3,3-trifluoropropionaldehyde (2.14 g, 19.1 mmol) and AcOH (1.09 mL, 19.1 mmol) followed by sodium cyanoborohydride (1.20 g, 19.1 mmol). The reaction was allowed to stir for 10 min., at which time the reaction was quenched with water (15 mL) then made basic with NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried and concentrated in vacuo to yield a white powder (3.3 g, 68%). Mass Spectrum: Calcd for C11H19NF3O2(M+H): 254. Found: 254.

Workup

  1. customwas quenched with water (15 mL)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e536e4a1244d4aa4bada2e3a7d86c6b6
Source dataset
uspto-grants-2014_11
Patent number
US08877761B2

Linked notes

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