Benzaldehyde → HCID 66653967, compound

HRID 920535Notes

Reaction equation

HRID 920535 reaction equation
[NH2:1][CH2:2][C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)([OH:5])[CH3:4].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH4-].[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:20]([NH:1][CH2:2][C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)([OH:5])[CH3:4])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 150366201-Amino-2-[4-(benzyloxy)phenyl]propan-2-ol

Product 1

HCID 66653967HCID 66653967, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-amino-2-(4-benzyloxy-phenyl)-propan-2-ol (1.26 g; 4.9 mmol), benzaldehyde (0.55 mL; 5.4 mmol), and p-toluenesulfonic acid (0.04 g; 0.24 mmol) in toluene (30 mL) was heated under reflux in a Dean-Stark apparatus, overnight. Subsequently, the mixture was cooled to RT and the solvent was removed in vacuo. The residue was suspended in MeOH (30 mL), cooled to −15° C., and treated with NaBH4 (0.74 g; 19.6 mmol), portionwise. After the addition was complete the mixture was warmed to RT and stirred for one hour. Subsequently, the MeOH was removed in vacuo. The residue was partitioned between Et2O and 5% aqueous NaHCO3. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 2:1) to give 1-benzylamino-2-(4-benzyloxy-phenyl)-propan-2-ol (1.07 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in a Dean-Stark apparatus, overnight
  3. customthe solvent was removed in vacuo
  4. temperaturecooled to −15° C.
  5. additionAfter the addition
  6. temperaturewas warmed to RT
  7. customSubsequently, the MeOH was removed in vacuo
  8. customThe residue was partitioned between Et2O and 5% aqueous NaHCO3
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by column chromatography (SiO2, Et2O:hexanes 2:1)

Sources & evidence

ORD record
ord-03db0ec0d0fe4644a6705f37e99f7f00
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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