Acetic Acid → HCID 57888629, compound

HRID 1820307Notes

Reaction equation

HRID 1820307 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O=[C:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.[CH3:29][C:30]1[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[C:31]=1[NH2:32].C(O)(=O)C.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:30]1([CH3:29])[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[C:31]=1[NH:32][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 69132,4,6-TrimethylanilineHCID 516892Sodium BicarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57888629HCID 57888629, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding sodium triacetoxyborohydride (7.98 g, 37.6 mmol) to a solution of tert-butyl 4-oxopiperidine-1-carboxylate (5.00 g, 25.1 mmol), 2,4,6-trimethylaniline (3.56 g, 26.3 mmol) and acetic acid (2.9 mL, 50.2 mmol) in methylene chloride (50 mL), the mixture was stirred at room temperature for 3.5 hours. Saturated aqueous sodium hydrogencarbonate (150 mL) was added to the reaction mixture, which was then stirred until bubbling settled. The organic layer was separated and the aqueous layer was extracted with chloroform (100 mL). The organic layers were combined, washed with saturated brine (100 mL) and dried (Na2SO4), and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (50 g Merck Art. 9385, hexane:ethyl acetate=9: 1) to obtain the title compound as a brown oil (5.71 g) (71% yield).

Workup

  1. stirringwas then stirred
  2. customuntil bubbling
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform (100 mL)
  5. washwashed with saturated brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (50 g Merck Art. 9385, hexane:ethyl acetate=9: 1)

Sources & evidence

ORD record
ord-27ead917c33842e3bbe4fcf29df228cc
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

Loading…