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Triethylamine → Benzyl 4-{2-[(trans-4-hydroxytetrahydrofuran-3-yl)oxy]ethoxy}piperidine-1-carboxylate

HRID 2359354
ノート
印刷プレビュー

反応式

HRID 2359354 の反応式
[OH:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.[O:21]1[CH:26]2[CH:22]1[CH2:23][O:24][CH2:25]2.C(N(CC)CC)C>ClCCl>[OH:21][C@@H:22]1[CH2:23][O:24][CH2:25][C@H:26]1[O:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:7][CH2:6]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 8471TriethylamineHCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 57517495Benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate

生成物 1

HCID 66990355Benzyl 4-{2-[(trans-4-hydroxytetrahydrofuran-3-yl)oxy]ethoxy}piperidine-1-carboxylate収率 49%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate (6.70 g, 24.0 mmol) produced in Reference Example 1 (1b) and 3,4-epoxytetrahydrofuran (1.03 g, 12.0 mmol) were dissolved in dichloromethane (5.0 mL). To the resulting mixture, a boron trifluoride diethyl ether complex (0.34 g, 2.4 mmol) was added at room temperature, followed by stirring for 16 hours. More boron trifluoride diethyl ether complex (0.34 g, 2.4 mmol) was added, followed by further stirring for two hours. Triethylamine (1.82 g, 18.0 mmol) was then added, and the resulting reaction liquid was directly purified by basic silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, ethyl acetate:methanol, 100:0-95:5, V/V) to give the desired title compound (2.14 g, yield 49%).

後処理

  1. additionTo the resulting mixture, a boron trifluoride diethyl ether complex (0.34 g, 2.4 mmol) was added at room temperature
  2. additionMore boron trifluoride diethyl ether complex (0.34 g, 2.4 mmol) was added
  3. stirringby further stirring for two hours
  4. customthe resulting reaction liquid
  5. customwas directly purified by basic silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, ethyl acetate:methanol, 100:0-95:5, V/V)

出典と根拠

ORDレコード
ord-7b35794fc397423fa349ad96b0dcca1e
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08685981B2

反応ノート

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