Ammonium Acetate → HCID 71239533, compound

HRID 1424274Notes

Reaction equation

HRID 1424274 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:7][CH:6]=1)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:24].[Na+]>CO>[NH2:24][CH:11]([C:8]1[CH:9]=[CH:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:17])=[CH:6][CH:7]=1)[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 68156788HCID 68156788, compound

Product 1

HCID 71239533HCID 71239533, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(3-Methyl-butyryl)-benzoic acid ethyl ester (2000 mg, 8.536 mM), ammonium acetate (6580 mg, 85.4 mM) and sodium cyanoborohydride (1070 mg, 17.1 mmol) in methanol (17.1 mL) was heated to 60° C. for 6 h. The reaction was cooled, quenched with NH4Cl solution (10 mL). MeOH was removed under reduced pressure. The aqueous solution was extracted with EtOAc (3×30 mL). The organic solution was separated, dried (Na2SO4) and concentrated. The crude material was separated by a 40 g HC silica gel column with 0-15% MeOH in DCM. The desired product was collected as colorless oily material (1560 mg, 77.7%). 1H NMR (500 MHz, CDCl3) δ ppm 0.91 (dd, J=13.66, 6.59 Hz, 6H) 1.40 (t, J=7.07 Hz, 3H) 1.84-1.99 (m, 3H) 4.27-4.42 (m, 3H) 6.36 (br. s., 2H) 7.51 (d, J=8.05 Hz, 2H) 8.05 (d, J=8.05 Hz, 2H). GC: m/z 235.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with NH4Cl solution (10 mL)
  3. customMeOH was removed under reduced pressure
  4. extractionThe aqueous solution was extracted with EtOAc (3×30 mL)
  5. customThe organic solution was separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude material was separated by a 40 g HC silica gel column with 0-15% MeOH in DCM
  9. customThe desired product was collected as colorless oily material (1560 mg, 77.7%)

Sources & evidence

ORD record
ord-ca2fc0faeaef40a1b21fe8229d709f16
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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