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

HRID 265017

反応式

HRID 265017 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). Mp: 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, [α]D21 32° (C=0.1;MeOH).

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

出典と根拠

ORDレコード
ord-ef9e7b7c20524272b8e8d7f1fee64ee9
出典データセット
uspto-grants-1997_07
特許番号
US05646309

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