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Sodium Bicarbonate → 1-[(5-Chloro-2-methoxy-3-pyridinyl)methyl]-4-[2-(cyclohexylmethyloxy)phenoxymethyl]piperidine

HRID 1837760
ノート
印刷プレビュー

反応式

HRID 1837760 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH:12]1([CH2:18][O:19][C:20]2[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=2[O:22][CH2:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][N:27]2[CH2:26][CH2:25][CH:24]([CH2:23][O:22][C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[O:19][CH2:18][CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH2:29][CH2:28]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=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 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 135677575-Chloro-2-methoxynicotinaldehydeHCID 178378784-[2-(Cyclohexylmethyloxy)phenoxymethyl]piperidine

生成物 1

HCID 226783551-[(5-Chloro-2-methoxy-3-pyridinyl)methyl]-4-[2-(cyclohexylmethyloxy)phenoxymethyl]piperidine収率 71%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒

実験手順

150 mg of 5-chloro-2-methoxy-3-pyridinecarboxaldehyde and 291 mg of 4-[2-(cyclohexylmethyloxy)phenoxymethyl]piperidine were dissolved in 5 ml of 1,2-dichloroethane. To the mixture were added 0.06 ml of acetic acid and 214 mg of sodium triacetoxyborohydride, followed by stirring at room temperature overnight. An aqueous saturated sodium bicarbonate was added to the reaction solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to give 285 mg of the title compound as a pale yellow oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-3d74263829e44d8b98bb18325e81d0f6
出典データセット
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06784192B2

反応ノート

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