Diethyl azodicarboxylate → 4-[3-(4-Ethoxycarbonyl-2-fluoro-phenoxy)-propyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 220840노트

반응식

HRID 220840 반응식
CCOC(/N=N/C(OCC)=O)=O.[CH2:13]([O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([F:24])[CH:18]=1)[CH3:14].[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][N:36]([CH2:39][CH2:40][CH2:41]O)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>O1CCCC1>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][N:36]([CH2:39][CH2:40][CH2:41][O:23][C:20]2[CH:21]=[CH:22][C:17]([C:16]([O:15][CH2:13][CH3:14])=[O:25])=[CH:18][C:19]=2[F:24])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

참가 물질

5

반응물 3

HCID 5462977Diethyl azodicarboxylateHCID 13745619Ethyl 3-fluoro-4-hydroxybenzoateHCID 162178001-Boc-4-(3-hydroxypropyl)piperazine

생성물 1

HCID 575554364-[3-(4-Ethoxycarbonyl-2-fluoro-phenoxy)-propyl]-piperazine-1-carboxylic acid tert-butyl ester수율 57%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triphenylphosphine polystyrene (loading 1.0 mmol/g, 11 g, 11.0 mmol) and DEAD (2.45 g, 11.0 mmol) were added to a solution of 3-fluoro-4-hydroxy-benzoic acid ethyl ester from Example E27 (1.3 g, 7.4 mmol) and 4-(3-hydroxy-propyl)-piperazine-1-carboxylic acid tert-butyl ester from Example E34 (1.8 g, 7.4 mmol) in tetrahydrofuran (100 ml) at 0° C. The suspension was allowed to warm to room temperature and stirred for 18 h. The mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAC) to yield the title compound (1.7 g, 57%).

후처리

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (eluant; EtOAC)

출처 및 근거

ORD 기록
ord-89c49444c53b4548901757dd7e5da571
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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