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Diethyl Ether → 4-Benzyl-1-(2-benzyloxycarbonylamino-ethyl)-piperidine-4-carboxylic acid ethyl ester

HRID 2223735
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HRID 2223735 반응식
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:19]([O:26][C:27](=[O:32])[NH:28][CH2:29][CH2:30]Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C.CCOCC>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][CH2:8][N:9]([CH2:30][CH2:29][NH:28][C:27]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:32])[CH2:10][CH2:11]1)=[O:5])[CH3:2]
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참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 278694benzyl N-(2-bromoethyl)carbamateHCID 53297794Ethyl 4-benzylpiperidine-4-carboxylate

생성물 1

HCID 597159294-Benzyl-1-(2-benzyloxycarbonylamino-ethyl)-piperidine-4-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
80 °C

실험 절차

4-Benzyl-piperidine-4-carboxylic acid ethyl ester (2.5 g, 10 mmol), (2-bromo-ethyl)-carbamic acid benzyl ester (2.58 g, 10 mmol) and DIPEA (1.7 mL, 10 mmol) are dissolved in THF (50 mL) and heated at 80° C. for 15 h. The mixture is poured into Et2O (200 mL) and washed with sat. Na2CO3 (50 mL). The ether phase is extracted with 1M aqueous HCl (3×50 mL), the aqueous extracts washed with ether (50 mL) and adjusted to pH 14 with cooled 33% aqueous NaOH. The aqueous phase is extracted with CH2Cl2 (4×50 mL). The organic extracts are dried (Na2SO4), filtered and evaporated to provide the title compound.

후처리

  1. washwashed with sat. Na2CO3 (50 mL)
  2. extractionThe ether phase is extracted with 1M aqueous HCl (3×50 mL)
  3. washthe aqueous extracts washed with ether (50 mL)
  4. temperaturewith cooled 33% aqueous NaOH
  5. extractionThe aqueous phase is extracted with CH2Cl2 (4×50 mL)
  6. dry with materialThe organic extracts are dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-6321cd404e1d42c98e78b5a8598096aa
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07375227B2

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