Fumaric Acid → 2-Amino-8-hydroxymethyl-8-chloro-1,2,3,4-tetrahydronaphthalene fumarate

HRID 375584ノート

反応式

HRID 375584 の反応式
[NH2:1][C:2]1(CO)[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([Cl:12])[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[C:15]([C@:23]([C:38]([OH:40])=[O:39])(O)[C@:24](C(=O)C1C=CC=CC=1)(O)[C:25]([OH:27])=[O:26])(=[O:22])C1C=CC=CC=1.C(O)(=O)/C=C/C(O)=O>C(O)C>[C:38]([OH:40])(=[O:39])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[CH:8]=[CH:7][CH2:6][C:5]([CH2:15][OH:22])([Cl:12])[C:4]=2[CH2:3]1

参加物

5

反応物 3

HCID 444972Fumaric AcidHCID 100133902-Amino-2-hydroxymethyl-8-chloro-1,2,3,4-tetrahydronaphthaleneHCID 12362977Di-benzoyl-d-tartaric acid

生成物 1

HCID 867492202-Amino-8-hydroxymethyl-8-chloro-1,2,3,4-tetrahydronaphthalene fumarate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

The expected product is obtained by resolving the compound obtained in stage D of Example 9 using (+)-dibenzoyl-D-tartaric acid by successive recrystallizations in ethanol. The enantiomeric purity is checked by chiral chromatography on a DIACEL-AD column, using an isopropanol/n-heptane/diethylamine mixture (40/1000/0.8) as eluent. The salt is then partitioned between 9N sodium hydroxide and dichloromethane. The aqueous phase is extracted with dichloromethane. After drying and evaporating the organic phases, the residue is dissolved in ethanol with one equivalent of fumaric acid and the mixture is brought to reflux. The expected product is then obtained after cooling, in the form of a white solid which is filtered off.

後処理

  1. customby successive recrystallizations in ethanol
  2. customThe salt is then partitioned between 9N sodium hydroxide and dichloromethane
  3. extractionThe aqueous phase is extracted with dichloromethane
  4. customAfter drying
  5. customevaporating the organic phases
  6. temperatureto reflux

出典と根拠

ORDレコード
ord-4dddc8347f1c4b08b74f867ac8c2bf7e
出典データセット
uspto-grants-1996_01
特許番号
US05486532

反応ノート

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