Carbon tetrabromide → HCID 56975661、化合物

HRID 1870250ノート

反応式

HRID 1870250 の反応式
O[CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:44].C(=O)([O-])O.[Na+]>ClCCl>[Br:44][CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1

参加物

6

反応物 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 11359478HCID 11359478、化合物

生成物 1

HCID 56975661HCID 56975661、化合物収率 79.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of (5S)-5-hydroxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (1.33 g), triphenylphosphine (2.10 g), carbon tetrabromide (2.65 g) and dichloromethane (50 ml) is stirred at room temperature for 30 minutes. The reaction solution is poured into a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with dichloromethane. The extract is dried over sodium sulfate, and concentrated under reduced pressure to remove the solvent, and the resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:n-hexane=4:1), and recrystallized from diethyl ether--n-hexane to give (5S)-5-bromomethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (1.26 g).

後処理

  1. extractionthe mixture is extracted with dichloromethane
  2. dry with materialThe extract is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto remove the solvent
  5. customthe resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:n-hexane=4:1)
  6. customrecrystallized from diethyl ether

出典と根拠

ORDレコード
ord-f2f374fca1894057a3166e98e8010bb5
出典データセット
uspto-grants-2000_08
特許番号
US06096736

反応ノート

読み込み中…