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Formylcycloheptane → N-[1-(Cycloheptylmethyl)piperidin-4-yl]-2-cyclopentyl-2-hydroxy-2-phenylacetamide

HRID 1289812
ノート
印刷プレビュー

反応式

HRID 1289812 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:22])[C:9]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)([OH:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.[CH:23]1([CH:30]=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.C(O)(=O)C>[CH:23]1([CH2:30][N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:22])[C:9]([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21]3)([OH:16])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:5][CH2:6]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 77961FormylcycloheptaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10662143N-(piperidin-4-yl)-2-cyclopentyl-2-hydroxy-2-phenylacetamide

生成物 1

HCID 10835518N-[1-(Cycloheptylmethyl)piperidin-4-yl]-2-cyclopentyl-2-hydroxy-2-phenylacetamide

試薬・触媒・溶媒 2

HCID 176
Acetic Acid
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

34 mg of N-(piperidin-4-yl)-2-cyclopentyl-2-hydroxy-2-phenylacetamide obtained in Step 2 of Example 27, 50 mg of cycloheptanecarbaldehyde and 10 mg of acetic acid were dissolved in tetrahydrofuran. 70 mg of sodium triacetoxyborohydride was added thereto and the resulting mixture was stirred for 17 hours. After the addition of a saturated aqueous solution of sodium bicarbonate, the reaction mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by preparative thin layer chromatography (Kieselgel™, 60F254, Art 5744 (manufactured by E. Merck; developing solvent: chloroform/methanol=10/1) to obtain the title compound.

後処理

  1. extractionthe reaction mixture was extracted with chloroform
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by preparative thin layer chromatography (Kieselgel™, 60F254, Art 5744 (manufactured by E. Merck; developing solvent: chloroform/methanol=10/1)

出典と根拠

ORDレコード
ord-eb7e7b4f620d4dc0b86fb8239145764a
出典データセット
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05750540

反応ノート

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