Sodium Hydroxide → Aplindore

HRID 1259465ノート

反応式

HRID 1259465 の反応式
CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([NH:19][CH2:20][C@@H:21]1[O:34][C:25]2=[C:26]3[C:30](=[CH:31][CH:32]=[C:24]2[O:23][CH2:22]1)[NH:29][C:28](=[O:33])[CH2:27]3)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>CC1CCCO1.C(O)C>[CH2:12]([NH:19][CH2:20][C@@H:21]1[O:34][C:25]2=[C:26]3[C:30](=[CH:31][CH:32]=[C:24]2[O:23][CH2:22]1)[NH:29][C:28](=[O:33])[CH2:27]3)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 86644796(2S)-2-[(benzylamino)methyl]-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one 4-methylbenzenesulfonate

生成物 1

HCID 158784Aplindore

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 73012-Methyltetrahydrofuran溶媒

実験手順

(2S)-2-[(benzylamino)methyl]-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one 4-methylbenzenesulfonate (0.75 g, 1.54 mmol) is suspended in 2-methyl tetrahydrofuran (10 mL), 1 N NaOH is added until the solids dissolve and the pH of the aqueous phase is 10 (pH paper), about 1.6 mL is required. The aqueous layer is removed, and the organic phase is washed with water (2×2 mL). The volatiles are removed by rotary evaporation to give a yellow syrup. The syrup is dissolved in absolute ethanol (3 mL) and evaporated to dryness. Absolute ethanol (3 mL) is added to the residue and removed by rotary evaporation to give crude (2S)-2-[(benzylamino)methyl]-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one as a yellow syrup which is carried directly into the next step.

後処理

  1. dissolutiondissolve
  2. customThe aqueous layer is removed
  3. washthe organic phase is washed with water (2×2 mL)
  4. customThe volatiles are removed by rotary evaporation
  5. customto give a yellow syrup
  6. customevaporated to dryness
  7. additionAbsolute ethanol (3 mL) is added to the residue
  8. customremoved by rotary evaporation

出典と根拠

ORDレコード
ord-d1c28b74ba064829bfe2662c34530531
出典データセット
uspto-grants-2013_06
特許番号
US08466296B2

反応ノート

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