Hydrochloric Acid → trans-1-[3-(Dimethylamino)propyl]-2-indanol

HRID 972720ノート

反応式

HRID 972720 の反応式
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.B.[OH-:17].[Na+].OO.Cl>O1CCCC1.O.C(O)C>[CH3:15][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C@H:7]1[OH:17]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 230024761(N,N-dimethylaminopropyl)indene

生成物 1

HCID 54288417trans-1-[3-(Dimethylamino)propyl]-2-indanol収率 81%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒3 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 20.6 g (0.10 mole) of 1-[3-(dimethylamino)-propyl]-indene in 100 ml of tetrahydrofuran is coold to 0° under nitrogen and 200 ml of 1M borane in tetrahydrofuran added over 30 minutes. After stirring overnight at ambient temperature the solution is cooled to 0° and the following added in the given order: 30 ml of water added cautiously, 170 ml of 10% sodium hydroxide solution and 32 ml of 30% hydrogen peroxide solution. After 1 hour at 0° the mixture is diluted with 1 liter of water and extracted with chloroform (3 × 400 ml) to give a white solid which is refluxed with 300 ml each of ethanol and 5% hydrochloric acid for 1 hour. After addition of 300 ml of water, 400 ml of distillate is collected. The residue is cooled, extracted with chloroform (200 ml, discard), basified with excess sodium hydroxide and extracted with chloroform (3 × 300 ml). Drying and solvent removal give 17.6 g of oil (81%, 1 spot on TLC).

後処理

  1. customis coold to 0° under nitrogen
  2. temperatureis cooled to 0°
  3. additionthe following added in the given order
  4. extractionextracted with chloroform (3 × 400 ml)
  5. customto give a white solid which
  6. customis collected
  7. temperatureThe residue is cooled
  8. extractionextracted with chloroform (200 ml, discard)
  9. extractionextracted with chloroform (3 × 300 ml)
  10. customDrying
  11. customsolvent removal

出典と根拠

ORDレコード
ord-6cadc94ff1a64be4aa81cf30aa73f535
出典データセット
uspto-grants-1977_10
特許番号
US04053596

反応ノート

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