Boron tribromide → (R)-5-Hydroxy-3-(N-isopropyl-N-n-propylamino)chroman

HRID 1684305ノート

反応式

HRID 1684305 の反応式
[CH:1]([N:4]([C@@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[O:18]C)[O:10][CH2:9]1)[CH2:5][CH2:6][CH3:7])([CH3:3])[CH3:2].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:18][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[CH2:17][C@@H:8]([N:4]([CH:1]([CH3:2])[CH3:3])[CH2:5][CH2:6][CH3:7])[CH2:9][O:10]2

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 10563531(R)-3-(N-isopropyl-N-n-propylamino)-5-methoxychroman

生成物 1

HCID 10848252(R)-5-Hydroxy-3-(N-isopropyl-N-n-propylamino)chroman収率 98%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-60 °C

実験手順

The HCl-salt of (R)-3-(N-isopropyl-N-n-propylamino)-5-methoxychroman (15.5 g, 52 mmol) was mixed with CH2Cl2 (100 mL) under nitrogen atmosphere and cooled to -60° C. BBr3 (27.2 g, 110 mmol) dissolved in CH2Cl2 (50 mL), was added slowly. The temperature was then raised to 0° C. and the reaction mixture was stirred at 0° C. for 12 h. The reaction mixture was then slowly added to a stirred saturated NaHCO3 solution. The layers were separated and the water layer was extracted once with CH2Cl2. The combined organic layers were dried (MgSO4). Removal of the solvent in vacuo gave the phenolic title compound. Yield: 98%. [α]D22 (Base)=-83.0° (C=0.1;MeOH) Mp(HCl-salt): 215°-222° C. (decomposes).

後処理

  1. additionwas added slowly
  2. temperatureThe temperature was then raised to 0° C.
  3. customThe layers were separated
  4. extractionthe water layer was extracted once with CH2Cl2
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. customRemoval of the solvent in vacuo

出典と根拠

ORDレコード
ord-ca341f2841c44563aef8619544f187d7
出典データセット
uspto-grants-1997_06
特許番号
US05639784

反応ノート

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