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

HRID 2359354
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HRID 2359354 반응식
[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
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 57517495Benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7b35794fc397423fa349ad96b0dcca1e
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08685981B2

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