Ethanol → (2S,3R)-3-amino-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octane di-p-toluoyl-D-tartrate salt

HRID 82428

反応式

HRID 82428 の反応式
[NH2:1][C@@H:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[C@H:3]1[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C(O)C.[C:20]1([CH3:47])[CH:25]=[CH:24][C:23]([C:26]([C@:28]([C:44]([OH:46])=[O:45])([OH:43])[C@:29]([C:34]([C:36]2[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=2)=[O:35])([OH:33])[C:30]([OH:32])=[O:31])=[O:27])=[CH:22][CH:21]=1>C(O)C.O>[C:20]1([CH3:47])[CH:25]=[CH:24][C:23]([C:26]([C@:28]([C:44]([OH:46])=[O:45])([OH:43])[C@:29]([C:34]([C:36]2[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=2)=[O:35])([OH:33])[C:30]([OH:32])=[O:31])=[O:27])=[CH:22][CH:21]=1.[NH2:1][C@@H:2]1[CH:7]2[CH2:6][CH2:5][N:4]([CH2:9][CH2:8]2)[C@H:3]1[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

参加物

5

反応物 3

HCID 702EthanolHCID 22860073(2R,3R)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acidHCID 25177374(2S,3R)-2-(Pyridin-3-ylmethyl)quinuclidin-3-amine

生成物 1

HCID 131729022(2S,3R)-3-amino-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octane di-p-toluoyl-D-tartrate salt収率 58.1%

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

実験手順

The (2S,3R)-3-amino-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octane was transferred to a clean 100 L reaction flask equipped with a mechanical stirrer, condenser, and temperature probe under an inert atmosphere. Ethanol (38.4 L) and di-p-toluoyl-D-tartaric acid (3.58 kg, 9.27 mol) were added. The reaction mixture was heated at gentle reflux for a minimum of 1 h. The reaction mixture was then stirred for a minimum of 12 h while it was cooled to between 15° C. and 30° C. The resulting suspension was filtered, and the filter cake was washed with ethanol (5.76 L). The filter cake was transferred to a clean 100 L glass reaction flask equipped with a mechanical stirrer, temperature probe, and condenser under an inert atmosphere. A 9:1 ethanol/water solution (30.7 L) was added, and the resulting slurry was heated at gentle reflux for a minimum of 1 h. The reaction mixture was then stirred for a minimum of 12 h while cooling to between 15° C. and 30° C. The mixture was filtered and the filter cake was washed with ethanol (5.76 L). The product was collected and dried under vacuum at 50° C.±5° C. for a minimum of 12 h to give 5.63 kg (58.1% yield) of (2S,3R)-3-amino-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octane di-p-toluoyl-D-tartrate salt.

後処理

  1. customequipped with a mechanical stirrer, condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureat gentle reflux for a minimum of 1 h
  4. temperaturewas cooled to between 15° C. and 30° C
  5. filtrationThe resulting suspension was filtered
  6. washthe filter cake was washed with ethanol (5.76 L)
  7. customThe filter cake was transferred to a clean 100 L glass reaction flask
  8. customequipped with a mechanical stirrer
  9. temperaturethe resulting slurry was heated
  10. temperatureat gentle reflux for a minimum of 1 h
  11. stirringThe reaction mixture was then stirred for a minimum of 12 h
  12. temperaturewhile cooling to between 15° C. and 30° C
  13. filtrationThe mixture was filtered
  14. washthe filter cake was washed with ethanol (5.76 L)
  15. customThe product was collected
  16. customdried under vacuum at 50° C.±5° C. for a minimum of 12 h

出典と根拠

ORDレコード
ord-71b7036609f848eab1da3ba2417c424d
出典データセット
uspto-grants-2014_09
特許番号
US08846715B2

関連ノート

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