Dichloromethane → HCID 22179417, compound

HRID 1016264Notes

Reaction equation

HRID 1016264 reaction equation
C([N:8](CC1C=CC=CC=1)[CH2:9][CH:10]([OH:21])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)C1C=CC=CC=1.ClCCl.C(=O)(O)[O-].[Na+].Cl[C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39]>[Pd].CO.O>[OH:21][CH:10]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH2:9][NH:8][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 3133123HCID 3133123, compound

Product 1

HCID 22179417HCID 22179417, compoundYield 80.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 1-[bisbenzylamino]-3-(4-methoxyphenoxy)propan-2-ol (1.26 g, 3.74 mmol), as prepared in the preceding step, 10% palladium on carbon (125 mg) and methanol (120 mL) was degassed under reduced pressure and refilled with H2 gas several times. After stirring under 1 atm H2 balloon at room temperature overnight, the mixture was filtered through Celite and washed with methanol. The filtrate was concentrated to a white solid (0.78 g, 100%). This solid (0.78 g, 3.96 mmol) was dissolved in methanol (20 mL), dichloromethane (20 mL), and water (10 mL). To this solution were added sodium bicarbonate (0.83 g, 9.88 mmol) and benzyl chloroformate (0.7 mL, 4.66 mmol) at room temperature. After stirring for 4 hours, the solution was concentrated and the residue was partitioned between dichloromethane and water. The organic layer was dried (Na2SO4), concentrated, and flash chromatographed on silica gel to give the title compound as a white solid (1.00 g, 80.8%). 1H NMR (CDCl3) δ 7.37-7.33 (m, 5H), 6.83 (s, 4H), 5.20 (m, 1H), 5.12 (s, 2H), 4.10 (m, 1H), 3.94-3.88 (m, 2H), 3.77 (s, 3H), 3.53-3.47 (m, 1H), 3.38-3.27 (m, 1H), 2.95 (m, 1H).

Workup

  1. customwas degassed under reduced pressure
  2. additionrefilled with H2 gas several times
  3. filtrationthe mixture was filtered through Celite
  4. washwashed with methanol
  5. concentrationThe filtrate was concentrated to a white solid (0.78 g, 100%)
  6. stirringAfter stirring for 4 hours
  7. concentrationthe solution was concentrated
  8. customthe residue was partitioned between dichloromethane and water
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. concentrationconcentrated
  11. customflash chromatographed on silica gel

Sources & evidence

ORD record
ord-3b4aeb5d4abd47b087ccaeb1f2e5a90d
Source dataset
uspto-grants-2002_11
Patent number
US06476016B2

Reaction notes

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