Acetone → (R)-3-(N-Isopropylamino)-5-methoxychroman

HRID 1684096

反応式

HRID 1684096 の反応式
[CH:1]([NH:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:15][CH3:16])[O:7][CH2:6]1)([CH3:3])[CH3:2].CC1C=CC(C(O[C@H](C(O)=O)[C@H](OC(C2C=CC(C)=CC=2)=O)C(O)=O)=O)=CC=1.C(O)C.CC(C)=O>CCOCC.[OH-].[K+]>[CH:1]([NH:4][C@@H:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:15][CH3:16])[O:7][CH2:6]1)([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 180AcetoneHCID 702EthanolHCID 263211Ditoluoyltartaric acid, (+)-HCID 19028181N-isopropyl-5-methoxychroman-3-amine

生成物 1

HCID 10489181(R)-3-(N-Isopropylamino)-5-methoxychroman収率 32%

試薬・触媒・溶媒 1

HCID 88018273KOH diethylether溶媒

反応条件

温度
20 °C

実験手順

The racemic 3-(N-isopropylamino)-5-methoxychroman (IV; 54 g, 0.224 mol) was mixed with an equimolar amount of (+)-di-1,4-toluoyl-D-tartaric acid (98.6 g, 0.244 mol). The mixture was dissolved in boiling ethanol (170 mL)/acetone (70 mL). The salt started to crystallize in the hot solvent mixture but was not filtered off until the solvent had cooled down to room temperature (20° C). The salt was then recrystallized nine times from ethanol acetone (1:5) to give the pure diastereomeric salt. Yield: 35% (54 g) (99% e.e). MD: 166°-168° C. The free enantiomer as the base (R)-3-(N-isopropylamino)-5-methoxychroman was obtained by the extraction of the salt in ether/KOH (1M). Yield: 32%, 17.5 g,

後処理

  1. dissolutionThe mixture was dissolved
  2. customto crystallize in the hot solvent mixture
  3. filtrationwas not filtered off until the solvent
  4. customThe salt was then recrystallized nine times from ethanol acetone (1:5)
  5. customto give the pure diastereomeric salt
  6. custom166°-168° C

出典と根拠

ORDレコード
ord-4f6541ad729246219f147f199a032e8c
出典データセット
uspto-grants-1997_06
特許番号
US05639772

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