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Formylcycloheptane → 1-(cycloheptyl-methyl)piperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate

HRID 1785249
ノート
印刷プレビュー

反応式

HRID 1785249 の反応式
[F:1][C:2]1([F:24])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]([O:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:9])[CH2:3]1.[CH:25]1([CH:32]=O)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[F:24][C:2]1([F:1])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:23])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:8]([O:10][CH:11]2[CH2:12][CH2:13][N:14]([CH2:32][CH:25]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:15][CH2:16]2)=[O:9])[CH2:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 77961FormylcycloheptaneHCID 5003444Sodium cyanoborohydrideHCID 69766623piperidin-4-yl(2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate

生成物 1

HCID 865973021-(cycloheptyl-methyl)piperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒
HCID 887
Methanol
溶媒
2 回
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 9.3 mg of piperidin-4-yl (2R)-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate in 1 ml of methanol, 10 mg of cycloheptanecarbaldehyde and then 0.5 ml of advancedly prepared 0.3 M methanol solution of sodium cyanoborohydride and zinc chloride (1:0.5) were added at room temperature, followed by 30 minutes' stirring at the same temperature. The reaction liquid was diluted with ethyl acetate, washed successively with saturated sodium hydrogenecarbonate solution and with saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the residue was purified on preparative thin layer chromatography (Kieselgel™60F254, Art5744 (Merck), chloroform/methanol=10/1) to provide the title compound.

後処理

  1. customThe reaction liquid
  2. washwashed successively with saturated sodium hydrogenecarbonate solution and with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationDistilling the solvent off under reduced pressure
  5. customthe residue was purified on preparative thin layer chromatography (Kieselgel™60F254, Art5744 (Merck), chloroform/methanol=10/1)

出典と根拠

ORDレコード
ord-9eddb3ba3f7b4b28b924fddb7597c338
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07504432B2

反応ノート

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