5-Fluoro-2-nitrophenol → (2S,4S)-1-tert-butyl 2-methyl 4-(5-fluoro-2-nitrophenoxy)pyrrolidine-1,2-dicarboxylate

HRID 240596

反応式

HRID 240596 の反応式
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][O:14][C:15](=[O:29])[C@@H:16]1[CH2:20][C@@H:19]([OH:21])[CH2:18][N:17]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].[F:30][C:31]1[CH:32]=[CH:33][C:34]([N+:38]([O-:40])=[O:39])=[C:35](O)[CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:30][C:31]1[CH:36]=[CH:35][C:34]([N+:38]([O-:40])=[O:39])=[C:33]([CH:32]=1)[O:21][C@@H:19]1[CH2:18][N:17]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C@H:16]([C:15]([O:14][CH3:13])=[O:29])[CH2:20]1

参加物

6

反応物 4

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 58413039(2S,4S)-1-tert-butyl 2-methyl 4-(5-fluoro-2-nitrophenoxy)pyrrolidine-1,2-dicarboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Diethylazodicarboxylate (1.76 ml) was added dropwise to a solution of N-Boc-trans-4-hydroxy-L-proline methyl ester (2.74 g), 5-fluoro-2-nitrophenol (1.47 g) and triphenylphosphine (2.93 g) in dichlormethane under cooling at 0° C. The coolant was removed after 20 min and the reaction mixture was stirred at room temperature over the weekend. The solvent was evaporated and the residue war purified by chromatography to give the desired product.

後処理

  1. customThe coolant was removed after 20 min
  2. customThe solvent was evaporated
  3. customthe residue war purified by chromatography

出典と根拠

ORDレコード
ord-c3706526ba5e40f2a807010243d86d46
出典データセット
uspto-grants-2014_02
特許番号
US08648068B2

関連ノート

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