Acetic Acid → HCID 57890363, compound

HRID 1819995Notes

Reaction equation

HRID 1819995 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:5][CH:4]=1)=O.[CH3:19][CH:20]1[CH2:24][CH2:23][CH2:22][NH:21]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1>[CH3:19][CH:20]1[CH2:24][CH2:23][CH2:22][N:21]1[CH2:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 130032-MethylpyrrolidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 17796625tert-Butyl [2-(4-formylphenyl)ethyl]carbamate

Product 1

HCID 57890363HCID 57890363, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-(4-formylphenyl)ethylcarbamate (3.0 g, 12.0 mmol), 2-methylpyrrolidine (1.44 ml, 14.4 mmol) and acetic acid (1.4 ml, 24.0 mmol) in THF (100 ml) was added sodium triacetoxyborohydride (5.1 g, 24.0 mmol), and the mixture was stirred at room temperature for 16 hrs. 10% Sodium hydrogencarbonate solution (100 ml) was added to the reaction solution, and the mixture was extracted with ethyl acetate (200 ml). The extract was washed with saturated brine, and dried over magnesium sulfate, and solvent was evaporated under reduced pressure. The residue was purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=4:1) to give the title compound (3.10 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (200 ml)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate, and solvent
  4. customwas evaporated under reduced pressure
  5. customThe residue was purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-85454743c87f4deebc91d93834b142a2
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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