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Ethyl 4-piperidinecarboxylate → Ethyl 1-{2-[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-(methyloxy)phenyl]ethyl}-4-piperidinecarboxylate

HRID 1942673
ノート
印刷プレビュー

反応式

HRID 1942673 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][N:15]=[C:14]([C:17]3[C:18]([O:26][CH3:27])=[C:19]([CH2:23][CH:24]=O)[CH:20]=[CH:21][CH:22]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[NH:28]1[CH2:33][CH2:32][CH:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][N:15]=[C:14]([C:17]3[C:18]([O:26][CH3:27])=[C:19]([CH2:23][CH2:24][N:28]4[CH2:33][CH2:32][CH:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:30][CH2:29]4)[CH:20]=[CH:21][CH:22]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]
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 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 58494089HCID 58494089、化合物

生成物 1

HCID 58494139Ethyl 1-{2-[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-(methyloxy)phenyl]ethyl}-4-piperidinecarboxylate収率 32.8%

試薬・触媒・溶媒 2

HCID 176Acetic Acid
触媒
HCID 6344Dichloromethane溶媒

実験手順

To a mixture of [3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-(methyloxy)phenyl]acetaldehyde (D103) (87.6 mg, 0.217 mmol) and ethyl 4-piperidinecarboxylate (137 mg, 0.870 mmol) in Dichloromethane (DCM) (5 mL) was added 3 drops of HOAc. The mixture was stirred at room temperature for 20 min. Then sodium triacetoxyborohydride (92 mg, 0.435 mmol) was added to the reaction mixture. The reaction mixture was stirred at room temperature overnight (16 h). The reaction was quenched with water. DCM was removed. The residue was extracted with EA (10 mL×3). The combined organic layers were dried over anhydrous sodium sulphate. After filtration and concentration, the residue was purified by column chromatography to afford ethyl 1-{2-[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-(methyloxy)phenyl]ethyl}-4-piperidinecarboxylate (D104) (38.7 mg). MS (ES): C28H34ClN3O4S requires 513.2. found 514.2 (M+H+).

後処理

  1. stirringThe reaction mixture was stirred at room temperature overnight (16 h)
  2. customThe reaction was quenched with water
  3. customDCM was removed
  4. extractionThe residue was extracted with EA (10 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-b52e8e7ace7c45cda9fcfe36e712c5df
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08389508B2

反応ノート

読み込み中…

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