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

HRID 220840ノート

反応式

HRID 220840 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-89c49444c53b4548901757dd7e5da571
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

反応ノート

読み込み中…