Methanol → Dexmethylphenidate

HRID 1860525

反応式

HRID 1860525 の反応式
[C:1]1([CH3:28])[C:2]([C:7]([C@:9]([C:25]([OH:27])=[O:26])([OH:24])[C@:10]([C:15]([C:17]2[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])([OH:14])[C:11]([OH:13])=[O:12])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.CO.[CH3:31][O:32][C:33]([C@@H:35]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C@@H:36]1[NH:41][CH2:40][CH2:39][CH2:38][CH2:37]1)=[O:34]>CC(C)=O>[C:1]1([CH3:28])[C:2]([C:7]([C@:9]([C:25]([O-:27])=[O:26])([OH:24])[C@:10]([C:15]([C:17]2[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])([OH:14])[C:11]([O-:13])=[O:12])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:31][O:32][C:33]([C@H:35]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C@@H:36]1[NH:41][CH2:40][CH2:39][CH2:38][CH2:37]1)=[O:34]

参加物

6

反応物 3

HCID 887MethanolHCID 6101852methyl (S)-phenyl((R)-piperidin-2-yl)acetateHCID 129858806(+)-di-toluoyl-D-tartaric acid

生成物 2

HCID 154101Dexmethylphenidate収率 121.5%HCID 131722594ditoluoyl-D-tartrate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Ditoluoyl-D-tartaric acid (5.033 g, 12.4 mmol) was suspended in a solution of 2% methanol in acetone (10 ml), and a solution of threo-methylphenidate (2.9 g, 12.4 mmol) in the same solvent (10 ml) was added. The solution was gently warmed to reflux whereupon all the reagents dissolved. The solution was immediately cooled and crystals began to form. The solution was allowed to stand at 4° C. for 17 hours and was then filtered. The crystals were washed with acetone (3×15 ml) and dried in vacuo to yield the ditoluoyl-D-tartrate salt of d-threo methylphenidate (3.516 g, 44.3% by weight; corresponding to 97% ee d-threo methylphenidate, as determined by chiral HPLC after salt cracking). The mother liquors were dried in vacuo to yield the ditoluoyl-D-tartrate salt of l-threo-methylphenidate as a solid, dry form (4.508 g, 50.5% yield, 88% ee).

後処理

  1. temperatureThe solution was gently warmed
  2. temperatureto reflux whereupon all the reagents
  3. dissolutiondissolved
  4. temperatureThe solution was immediately cooled
  5. customto form
  6. filtrationwas then filtered
  7. washThe crystals were washed with acetone (3×15 ml)
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-2759d53622de4762bbfd2cadc66d7f14
出典データセット
uspto-grants-2003_03
特許番号
US06531489B2

関連ノート

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