Benzaldehyde → HCID 69818187, compound

HRID 2417414Notes

Reaction equation

HRID 2417414 reaction equation
[NH2:1][C@H:2]([CH2:19][OH:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1>[CH2:21]([NH:1][C@H:2]([CH2:19][OH:20])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:9]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 69818058HCID 69818058, compound

Product 1

HCID 69818187HCID 69818187, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-N-[4-(2-amino-3-hydroxypropyl)phenyl)benzamide (207 mg) and benzaldehyde (106 mg) in 1,4-dioxane (5 ml) was refluxed for 3 hours, and the mixture was evaporated in vacuo. To the residue in methanol (5 ml) was added sodium borohydride (15 mg) on ice-cooling, and stirred at the same temperature for 1 hour. The resulting mixture was poured into saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel to afford (S)-N-[4-[2-(benzylamino)-3-hydroxypropyl]phenyl]benzamide (250 mg) as colorless oil.

Workup

  1. customthe mixture was evaporated in vacuo
  2. additionTo the residue in methanol (5 ml) was added sodium borohydride (15 mg) on ice-
  3. temperaturecooling
  4. additionThe resulting mixture was poured into saturated aqueous sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was chromatographed (hexane-ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-523406fd444243aeb35790f475e5e8f9
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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