Potassium Hydroxide → 8-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 30533ノート

反応式

HRID 30533 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.C1C=CC=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[NH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][CH: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 230669958-Amino-1,2,3,4-tetrahydronaphthalen-2-ol収率 65%

試薬・触媒・溶媒 2

HCID 10962144Benzeneruthenium(II) Chloride Dimer触媒HCID 3776Isopropanol溶媒3 回

反応条件

温度
45 °C

実験手順

To a stirred solution of benzeneruthenium (II) chloride dimer (3.10 mg, 0.006 mmol) and (1S, 2R)-(−)-cis-1-amino-2-indanol (3.7 mg, 0.025 mmol) in degassed isopropanol was heated at 80° C. for 20 minutes under argon. The mixture was added to the solution of 8-amino-3,4-dihydro-1H-naphthalen-2-one (50 mg, 0.310 mmol) in isopropanol (3 mL) at room temperature. A solution of potassium hydroxide (3.48 mg, 0.062 mmol) in isopropanol (1 mL) was added, and the mixture was stirred at 45° C. for 1 hour. The mixture was passed through silica gel and washed with ethyl acetate. The filtrate was concentrated under reduced pressure to afford the chiral 8-amino-1,2,3,4-tetrahydro-naphthalen-2-ol enantiomer (33.0 mg, 65% yield).

後処理

  1. washwashed with ethyl acetate
  2. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-b2d7cb3d3f5948ad946ce13a476fe62f
出典データセット
uspto-grants-2008_09
特許番号
US07423175B2

反応ノート

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