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Methanol → 1-(1-benzyloxycarbonylpiperidin-4-yl)-1H-indole-6-carboxylic acid

HRID 494911
ノート
印刷プレビュー

反応式

HRID 494911 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([O:28]C)=[O:27])[CH:24]=3)[CH:19]=[CH:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([OH:28])=[O:27])[CH:24]=3)[CH:19]=[CH:18]2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 57682829methyl 1-(1-benzyloxycarbonylpiperidin-4-yl)-1H-indole-6-carboxylate

生成物 1

HCID 576829061-(1-benzyloxycarbonylpiperidin-4-yl)-1H-indole-6-carboxylic acid収率 87.1%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

90.0 g of methyl 1-(1-benzyloxycarbonylpiperidin-4-yl)-1H-indole-6-carboxylate was dissolved in a mixed solution consisting of 760 ml of methanol and 200 ml of tetrahydrofuran. Thereafter, 92 ml of a 5 N sodium hydroxide aqueous solution was added to the reaction solution, and the mixture was then heated to a temperature between 60° C. and 70° C. After completion of the reaction, the reaction solution was cooled, and 65.0 g of ammonium chloride was added thereto, followed by concentration under a reduced pressure. A 5% KHSO4 aqueous solution was added to the residue, so as to adjust pH to be 5 to 6, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. Thereafter, the residue was solidified, and then collected from a mixed solvent consisting of hexane and t-butylmethyl ether by filtration, so as to obtain 75.6 g of the subject compound.

後処理

  1. temperaturethe mixture was then heated to a temperature between 60° C. and 70° C
  2. customAfter completion of the reaction
  3. temperaturethe reaction solution was cooled
  4. concentrationfollowed by concentration under a reduced pressure
  5. additionA 5% KHSO4 aqueous solution was added to the residue
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materiala saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate
  9. customAfter removing the drying agent
  10. filtrationby filtration
  11. concentrationthe organic layer was concentrated under a reduced pressure
  12. customcollected from a mixed solvent
  13. filtrationconsisting of hexane and t-butylmethyl ether by filtration

出典と根拠

ORDレコード
ord-2d6025b98000440eb5e73734c5cfb996
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07538123B2

反応ノート

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