Methanol → Dexmethylphenidate

HRID 1374130

반응식

HRID 1374130 반응식
[CH3:1][O:2][C:3]([C@@H:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@@H:6]1[NH:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:4].[C:18]1([CH3:45])[C:19]([C:24]([C@:26]([C:42]([OH:44])=[O:43])([OH:41])[C@:27]([C:32]([C:34]2[C:35]([CH3:40])=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:33])([OH:31])[C:28]([OH:30])=[O:29])=[O:25])=[CH:20][CH:21]=[CH:22][CH:23]=1.CO>CC(C)=O>[C:18]1([CH3:45])[C:19]([C:24]([C@:26]([C:42]([O-:44])=[O:43])([OH:41])[C@:27]([C:32]([C:34]2[C:35]([CH3:40])=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:33])([OH:31])[C:28]([O-:30])=[O:29])=[O:25])=[CH:20][CH:21]=[CH:22][CH:23]=1.[CH3:1][O:2][C:3]([C@H:5]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C@@H:6]1[NH:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:4]

참가 물질

6

반응물 3

HCID 887MethanolHCID 6101852methyl (S)-phenyl((R)-piperidin-2-yl)acetate2회HCID 129858806(+)-di-toluoyl-D-tartaric acid

생성물 2

HCID 154101Dexmethylphenidate수율 97%HCID 131722594ditoluoyl-D-tartrate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Resolve dl-threo-methylphenidate by the procedure described in the Example of PCT/GB97/00185 (International Publication No. WO 97/27176): 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 vacuc 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).

후처리

  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 vacuc

출처 및 근거

ORD 기록
ord-eb4b30fa4fec40fdb01f055860b52701
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07164025B2

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