Water → 3-Amino-3-(3,4-dimethoxyphenyl)propan-1-ol

HRID 1941237Notes

Reaction equation

HRID 1941237 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)[CH2:3][C:4]([O-])=[O:5].[BH4-].[Na+].C(OCC)(=O)C.CCCCCC.O>CO>[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)[CH2:3][CH2:4][OH:5]

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 22282520HCID 22282520, compound

Product 1

HCID 37392353-Amino-3-(3,4-dimethoxyphenyl)propan-1-olYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-amino-3-(3',4'-dimethoxyphenyl)-propionate (4.12 grams, 17.2 mmol) in methanol (50 milliliters) was slowly added to stirred sodium borohydride (6.51 grams, 17.2 mmol). After the initial effervescence had ceased the mixture was refluxed for 1 hour. Reaction progress was monitored by TLC (20% ethyl acetate/hexane, uv) and was complete after 1 hour. The reaction mixture was allowed to cool and then 20 milliliters of water was added. The methanol was removed in vacuo resulting in the formation of a gum which was extracted into methylene chloride (3×20 milliliters). The combined extracts were dried over magnesium sulfate and concentrated to afford an oil which was refrigerated. A waxy solid formed which was dried in vacuo (60° C.,<1 mm) to afford 3.30 g (86%) of the product as a white solid. 1H NMR (CDCl13)δ6.91-6.78(m, 3H), 4.15-4.04(m, 1H), 3.89(s, 3H), 3.88(s, 3H), 3.84-3.71(s, 2H), 3.91-2.45(broad m, 1H), 1.95-1.78(m, 2H).

Workup

  1. temperaturewas refluxed for 1 hour
  2. customReaction progress
  3. temperatureto cool
  4. customThe methanol was removed in vacuo
  5. customresulting in the formation of a gum which
  6. extractionwas extracted into methylene chloride (3×20 milliliters)
  7. dry with materialThe combined extracts were dried over magnesium sulfate
  8. concentrationconcentrated
  9. customto afford an oil which
  10. customA waxy solid formed which
  11. customwas dried in vacuo (60° C.,<1 mm)

Sources & evidence

ORD record
ord-2de46391378d4483b8d74086f093feab
Source dataset
uspto-grants-1997_12
Patent number
US05703098

Reaction notes

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