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

HRID 1941237ノート

反応式

HRID 1941237 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2de46391378d4483b8d74086f093feab
出典データセット
uspto-grants-1997_12
特許番号
US05703098

反応ノート

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