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Methanesulfonyl chloride → Ethyl N-tert-butoxycarbonyl-4-(3-methane-sulfonylaminobenzyl)piperidine-4-carboxylate

HRID 1068452
ノート
印刷プレビュー

反応式

HRID 1068452 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=2)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29][S:30](Cl)(=[O:32])=[O:31]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][S:30]([CH3:29])(=[O:32])=[O:31])[CH:21]=2)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 53931544ethyl N-tert-butoxycarbonyl-4-(3-nitrobenzyl)piperidine-4-carboxylate

生成物 1

HCID 21193321Ethyl N-tert-butoxycarbonyl-4-(3-methane-sulfonylaminobenzyl)piperidine-4-carboxylate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

A mixture of ethyl N-tert-butoxycarbonyl-4-(3-nitrobenzyl)-piperidine-4-carboxylate (0.85 g, 2.17 mmol; Example 69, Step A) and 5% palladium on charcoal (0.06 g) in ethanol (100 mL) was hydrogenated at room temp. at 50 psi overnight. The resultant mixture was filtered through a plug of Celite, and the filtrate was concentrated under vacuum. The residue was dissolved in pyridine (5 mL), treated with methanesulfonyl chloride (0.24 mL, 3.2 mmol), and heated at 60° C. for 3 h. The product mixture was concentrated under vacuum, and the residue was subjected to column chromatography on silica gel eluting with 2% methanol in chloroform. Collection and concentration of appropriate fractions provided the title compound.

後処理

  1. customwas hydrogenated at room temp. at 50 psi overnight
  2. filtrationThe resultant mixture was filtered through a plug of Celite
  3. concentrationthe filtrate was concentrated under vacuum
  4. dissolutionThe residue was dissolved in pyridine (5 mL)
  5. concentrationThe product mixture was concentrated under vacuum
  6. customCollection and concentration of appropriate fractions

出典と根拠

ORDレコード
ord-37216a9de38a4250be0ef2446c785eca
出典データセット
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06248756B1

反応ノート

読み込み中…

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