Glycolaldehyde dimer → Ethyl 2-[4-(2-hydroxyethylamino)phenyl]propionate

HRID 1274987Notes

Reaction equation

HRID 1274987 reaction equation
[CH2:1]1OC(O)C[O:3][CH:2]1O.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=1.[BH3-][C:23]#N.[Na+]>CC#N>[OH:3][CH2:2][CH2:1][NH:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]([CH3:21])[C:17]([O:19][CH2:20][CH3:23])=[O:18])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 186078Glycolaldehyde dimerHCID 3016109Methyl 2-(4-aminophenyl)propionateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 22118659Ethyl 2-[4-(2-hydroxyethylamino)phenyl]propionate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the procedure of Himmelsbach, et. al., EP 0587134, Example V, glycolaldehyde dimer (Aldrich) (1 mmol) is added to a solution of methyl 2-(4-aminophenyl)propionate (1 mmol) in aqueous CH3CN (pH 6-7) (10 mL), followed by NaBH3CN (1.2 mmol), and the mixture is allowed to stir for 1 h. The mixture concentrated to an oil, and the residue is dissolved in a mixture of ice water and EtOAc. The aqueous layer is neutralized with 4N NaOH and washed with EtOAc. The organic phase is concentrated to an oil. A solution of the oil in EtOAc is chromatographed (silica gel, gradient, 5-30% CH3OH/CH2Cl2 -0.1% HOAc). The fractions containing the product are combined and concentrated to give the title compound.

Workup

  1. concentrationThe mixture concentrated to an oil
  2. dissolutionthe residue is dissolved in a mixture of ice water and EtOAc
  3. washwashed with EtOAc
  4. concentrationThe organic phase is concentrated to an oil
  5. customA solution of the oil in EtOAc is chromatographed (silica gel, gradient, 5-30% CH3OH/CH2Cl2 -0.1% HOAc)
  6. additionThe fractions containing the product
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2440400fb1b84b7294d50909f6adc886
Source dataset
uspto-grants-2000_12
Patent number
US06159964

Reaction notes

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