Potassium Hydroxide → (2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol

HRID 1432831ノート

反応式

HRID 1432831 の反応式
C1C2C(=CC=CC=2)[C@H](N)[C@@H]1O.[NH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2.[OH-].[K+]>C(O)(C)C.C1C=CC=CC=1.Cl[Ru]Cl>[NH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]2

参加物

6

反応物 3

HCID 14797Potassium HydroxideHCID 9866743(1S,2R)-(-)-1-Amino-2-indanolHCID 230669938-Amino-3,4-dihydro-1H-naphthalen-2-one

生成物 1

HCID 57936087(2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol収率 56%

試薬・触媒・溶媒 2

HCID 11096978HCID 11096978、化合物触媒HCID 3776Isopropanol溶媒3 回

実験手順

A stirred solution benzeneruthenium(II) chloride dimmer (1.55 g) and (1S, 2R)-(−)-cis-1-amino-2-indanol (1.85 g) in degassed isopropanol (500 ml) was heated at 80° C. for 20 minutes under argon, and then cooled to room temperature. The mixture was added to the solution of 8-amino-3,4-dihydro-1H-naphthalen-2-one (25.0 g) in isopropanol (700 ml) at room temperature followed by the prepared solution of potassium hydroxide (1.74 g) in 300 ml of isopropanol (pre-prepared at 45° C. to dissolve and then cooled to room temperature). After stirred at 45° C. for 30 minutes, the mixture was cooled to room temperature and was passed through silica gel pad and washed with ethylacetate. The filtrate was concentrated under reduced pressures and the obtained solid was dissolved in dichloromethane and treated with activated charcoal for 10 minutes. After filtered through a silica gel pad, the mixture was concentrated under reduced pressure. The obtained product was recrystallized from dichloromethane to afford red crystal, of (R)-8-amino-1,2,3,4-tetrahydro-naphthalen-2-ol (14 g, 56% yield).

後処理

  1. custompre-prepared at 45° C.
  2. dissolutionto dissolve
  3. temperaturecooled to room temperature)
  4. temperaturethe mixture was cooled to room temperature
  5. washwashed with ethylacetate
  6. concentrationThe filtrate was concentrated under reduced pressures
  7. dissolutionthe obtained solid was dissolved in dichloromethane
  8. additiontreated with activated charcoal for 10 minutes
  9. filtrationAfter filtered through a silica gel pad
  10. concentrationthe mixture was concentrated under reduced pressure
  11. customThe obtained product was recrystallized from dichloromethane
  12. customto afford red crystal

出典と根拠

ORDレコード
ord-b174e98179204ea480eb6c9eeea13b36
出典データセット
uspto-grants-2009_11
特許番号
US07612113B2

反応ノート

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