Acetic Acid → HCID 70874194, compound

HRID 2208833Notes

Reaction equation

HRID 2208833 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]([CH3:20])=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21](=O)[CH3:22].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.O>[CH2:1]([N:8]([CH2:21][CH3:22])[C:9]1[C:10]([CH3:20])=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 5127212HCID 5127212, compound

Product 1

HCID 70874194HCID 70874194, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of ethyl 3-(benzylamino)-2-methylbenzoate (396 mg, 1.47 mmol) in DCE (10 ml) was added acetaldehyde (164 μl, 2.94 mmol) followed by acetic acid (0.17 ml, 2.94 mmol) The reaction was stirred at room temperature for 10 min and then sodium triacetoxyborohydride (0.62 g, 2.94 mmol) was added and the reaction stirred for 16 h. Distilled water (30 ml) was added and solid NaHCO3 was then added until the aqueous phase was pH7, the phases were separated, the aqueous phase was washed with DCM (2×50 ml), the combined organics were then washed with brine (50 ml), dried using Na2SO4, filtered and evaporated. The resultant residue was then purified using a 25 g silica Isolute column eluting using a gradient of 0% to 5% EtOAc in heptane to afford the title compound as a colourless oil (372 mg, 81%). LC-MS 94%, m/z=298.1, 1H NMR (500 MHz, Chloroform-d) δ 7.48 (dd, J=7.5, 1.3 Hz, 1H), 7.29-7.08 (m, 8H), 4.32 (q, J=7.1 Hz, 2H), 4.05 (s, 2H), 2.92 (q, J=7.1 Hz, 2H), 2.56 (s, 3H), 1.35 (t, J=7.1 Hz, 3H), 0.92 (t, J=7.1 Hz, 3H).

Workup

  1. stirringthe reaction stirred for 16 h
  2. customthe phases were separated
  3. washthe aqueous phase was washed with DCM (2×50 ml)
  4. washthe combined organics were then washed with brine (50 ml)
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe resultant residue was then purified
  9. washeluting

Sources & evidence

ORD record
ord-b6101b9c0ce149ee801f26c23227c8c8
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

Loading…