L-Tartaric acid → D-Tartaric acid

HRID 374551

反応式

HRID 374551 の反応式
C(N1C[C@@H]2[C@@H](CCCN2)C1)C1C=CC=CC=1.[C:17]([OH:26])(=[O:25])[C@@H:18]([C@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19].C([C@@H]([C@H](C(O)=O)O)O)(O)=O.C(N1C[C@H]2[C@H](CCCN2)C1)C1C=CC=CC=1>CN(C)C=O>[C:17]([OH:26])(=[O:25])[C@H:18]([C@@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19]

参加物

5

反応物 3

HCID 444305L-Tartaric acidHCID 10198297(4aS-cis-)-6-benzyl-octahydropyrrolo(3.4-b)pyridineHCID 68615090[R,R]-8-benzyl-2,8-diazabicyclo[4.3.0]nonane L-tartrate

生成物 1

HCID 439655D-Tartaric acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
18 °C

実験手順

73.6 g (0.34 mol) of cis-8-benzyl-2,8-diazabicyclo[4.3.0]nonane, as a solution in 111 ml of dimethylformamide, are added dropwise, at 80° to 90° C., to a solution of 102.9 g (0.685 mol) of L(+)-tartaric acid in 343 ml of dimethylformamide. Seeding with [R,R]-8-benzyl-2,8-diazabicyclo[4.3.0]nonane L-tartrate takes place, and the mixture is cooled slowly down to an internal temperature of 18° C. The crystals are filtered off with suction, and the filtrate is seeded with [S,S]-8-benzyl-2,8-diazabicyclo[4.3.0]nonane L-tartrate and stirred until crystallisation is complete. (After concentrating and liberating the base as described under method I, [S,S]-8-benzyl-2,8-diazabicyclo[4.3.0]nonane D-tartrate can be obtained from the mother liquor by purification with D(-)-tartaric acid.) Subsequently, filtration takes place with suction, and the sediment is washed with dimethylformamide and isopropanol and air-dried. The crystals are recrystallised from 88% strength ethanol. 52 g of [S,S] -8-benzyl-2,8-diazabicyclo[4.3.0]nonane L-tartrate trihydrate are obtained.

後処理

  1. filtrationThe crystals are filtered off with suction
  2. concentration(After concentrating

出典と根拠

ORDレコード
ord-dcfbf7dddfc947139680bf75f0b1802e
出典データセット
uspto-grants-1996_01
特許番号
US05480879

関連ノート

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