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

HRID 1941237노트

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HRID 1941237 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 222825203-Amino-3-(3',4'-dimethoxyphenyl)-propionate

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2de46391378d4483b8d74086f093feab
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05703098

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