Benzenepropanal → HCID 54396813, compound

HRID 1952961Notes

Reaction equation

HRID 1952961 reaction equation
[NH2:1][C@@H:2]([C:5]([NH2:7])=[O:6])[CH2:3][OH:4].[C:8]1([CH2:14][CH2:15][CH:16]=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H][H]>CO.[Pd]>[OH:4][CH2:3][C@@H:2]([NH:1][CH2:16][CH2:15][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([NH2:7])=[O:6]

Participants

6

Reactant 3

HCID 7707BenzenepropanalHCID 447822D-serine amideHCID 178418361HCID 178418361, compound

Product 1

HCID 54396813HCID 54396813, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

D-Serinamide (0.038 moles, 4 g) and 3-phenylpropanal (0.038 moles, 5.1 g) are dissolved in methanol (400 ml) in a Parr bottle and hydrogenated in the presence of 10% Pd/C (3 g) at 40 psi, until hydrogen absorption ceases. The catalyst is filtered off and the solution is evaporated to dryness under vacuum, taken up in ethyl acetate (300 ml) and washed with water (2×200 ml). The organic phase is dried and dissolved in warm ethyl ether (300 ml) to precipitate the product as a white solid by slow evaporation of the solvent at r.t. Yield: 3.8 g (45%)--m.p.=76-78° C. [α]589 (c=1, methanol)=+13.2°

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solution is evaporated to dryness under vacuum
  3. washwashed with water (2×200 ml)
  4. customThe organic phase is dried
  5. dissolutiondissolved in warm ethyl ether (300 ml)
  6. customto precipitate the product as a white solid
  7. customby slow evaporation of the solvent at r.t
  8. customm.p.=76-78° C. [α]589 (c=1, methanol)=+13.2°

Sources & evidence

ORD record
ord-758e75571ff54873b8256f44713220ed
Source dataset
uspto-grants-2000_09
Patent number
US06114391

Reaction notes

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