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Sodium cyanoborohydride → (1S,2S)-2-[(E)-3-(4-Acetylamino-4-phenyl-piperidin-1-yl)-propenyl]-1-(3,4-dichloro-phenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide

HRID 1172223
ノート
印刷プレビュー

反応式

HRID 1172223 の反応式
[C:1]1([C:7]2([NH:13][C:14](=[O:16])[CH3:15])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:17][C:18]1[CH:43]=[CH:42][C:21]([CH2:22][N:23]([CH3:41])[C:24]([C@@:26]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=3)[CH2:28][C@H:27]2/[CH:29]=[CH:30]/[CH:31]=O)=[O:25])=[CH:20][CH:19]=1.C([BH3-])#N.[Na+]>C(O)C>[F:17][C:18]1[CH:43]=[CH:42][C:21]([CH2:22][N:23]([CH3:41])[C:24]([C@@:26]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=3)[CH2:28][C@H:27]2/[CH:29]=[CH:30]/[CH2:31][N:10]2[CH2:11][CH2:12][C:7]([NH:13][C:14](=[O:16])[CH3:15])([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9]2)=[O:25])=[CH:20][CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 15886675N-(4-Phenylpiperidin-4-yl)acetamideHCID 86609590(1S,2S)-1-(3,4-Dichloro-phenyl)-2-((E)-3-oxo-propenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide

生成物 1

HCID 67423469(1S,2S)-2-[(E)-3-(4-Acetylamino-4-phenyl-piperidin-1-yl)-propenyl]-1-(3,4-dichloro-phenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒
2 回

実験手順

N-(4-Phenyl-piperidin-4-yl)-acetamide (140 mg, 0.64 mmol) dissolved in ethanol (3 ml) is added to (1S,2S)-1-(3,4-Dichloro-phenyl)-2-((E)-3-oxo-propenyl)-cyclopropanecarboxylic acid (4-fluoro-benzyl)-methyl-amide dissolved in ethanol (5 ml) followed by dropwise addition of sodium cyanoborohydride (1.0M in THF, 1.97 ml, 1.97 mmol) at 0° C. After complete addition the mixture is kept at ambient temperature for 2 hours. The reaction is quenched by addition of sodium bicarbonate (3 ml, sat.) and the ethanol is removed by means of evaporation. Ethyl acetate (30 ml) is added to the remanence. The organic fraction is washed successively with sodium bicarbonate (10 ml, sat.) and brine (10 ml, sat.), dried (MgSO4) and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with ethyl acetate:ethanol:triethylamine (95:0:5)-(90:5:5) to furnish the title compound as an oil. Yield 81 mg (27%). LC/MS (m/z) 610.3 (M+H+).

後処理

  1. additionAfter complete addition the mixture
  2. customThe reaction is quenched by addition of sodium bicarbonate (3 ml, sat.)
  3. customthe ethanol is removed by means of evaporation
  4. additionEthyl acetate (30 ml) is added to the remanence
  5. washThe organic fraction is washed successively with sodium bicarbonate (10 ml, sat.) and brine (10 ml, sat.)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel chromatography
  9. washeluting with ethyl acetate:ethanol:triethylamine (95:0:5)-(90:5:5)

出典と根拠

ORDレコード
ord-b7c10c9369f745fb96e72181082299de
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07834008B2

反応ノート

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