Furfural → HCID 59625650, compound

HRID 2192841Notes

Reaction equation

HRID 2192841 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[NH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[C:19]([N:21]([CH2:35][CH:36]([CH3:38])[CH3:37])[CH:22]1[CH2:27][CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]1)=[O:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:12]=[CH:11][C:10]=1[C:19]([N:21]([CH2:35][CH:36]([CH3:38])[CH3:37])[CH:22]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]1)=[O:20]

Participants

6

Reactant 4

HCID 7362FurfuralHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59625513HCID 59625513, compound

Product 1

HCID 59625650HCID 59625650, compoundYield 3.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Furaldehyde (0.20 g) and tert-butyl 3-[{[2-amino-4-(trifluoromethyl)phenyl]carbonyl}(2-methylpropyl)amino]piperidine-1-carboxylate (0.33 g) were dissolved in acetic acid (5.0 ml), sodium triacetoxyborohydride (0.31 g) was added and the mixture was stirred at room temperature overnight. The reaction mixture was basified with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (0:10→10:0) was concentrated under reduced pressure. The residue was dissolved in trifluoroacetic acid (2 ml), and the mixture was stirred for 30 min. The reaction mixture was concentrated and purified by HPLC to give the object compound (12.2 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe fraction eluted with ethyl acetate-hexane (0:10→10:0)
  6. concentrationwas concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in trifluoroacetic acid (2 ml)
  8. stirringthe mixture was stirred for 30 min
  9. concentrationThe reaction mixture was concentrated
  10. custompurified by HPLC

Sources & evidence

ORD record
ord-634e95667ff946ebbec9ba54a6f9e9de
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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