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Triethylamine → 4-[3-(4-Hydroxymethyl-piperidin-1-YL)-pyrazin-2-YL]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1850260
ノート
印刷プレビュー

反応式

HRID 1850260 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19](Cl)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH2:26][CH2:25][CH:24]([CH2:27][OH:28])[CH2:23][CH2:22]1.CCN(CC)CC>CS(C)=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([CH2:27][OH:28])[CH2:23][CH2:22]3)=[N:18][CH:17]=[CH:16][N:15]=2)[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

6

反応物 3

HCID 8471TriethylamineHCID 4207714-PiperidinemethanolHCID 58547013Tert-butyl 4-(3-chloropyrazin-2-yl)piperidine-1-carboxylate

生成物 1

HCID 585475224-[3-(4-Hydroxymethyl-piperidin-1-YL)-pyrazin-2-YL]-piperidine-1-carboxylic acid tert-butyl ester収率 80.32%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒
HCID 962
Water
溶媒

反応条件

温度
100 °C

実験手順

To a solution of 4-(3-chloro-pyrazin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (39) (297 mg, 1 mmol) and piperidin-4-yl-methanol (35) (126.5 mg, 1.1 mmol) in DMSO (6 mL) was added Et3N (202 mg, 2 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (30 mL×3). The combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel to give compound (40) (302 mg, 0.8 mmol, yield 80.32%).

後処理

  1. extractionextracted with EtOAc (30 mL×3)
  2. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel

出典と根拠

ORDレコード
ord-8c7b4393dd6a4baf9e4fe21211a1deeb
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08957073B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート