Triphenylphosphine → Quinoxaline

HRID 240240

反応式

HRID 240240 の反応式
O[C@@H:2]1[CH2:6][N:5]([C:7](OC(C)(C)C)=O)[C@H:4]([C:14](OC)=O)[CH2:3]1.[C:18]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:37]([C:45](OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[N:37]1[C:3]2[C:4](=[CH:14][CH:18]=[CH:6][CH:2]=2)[N:5]=[CH:7][CH:45]=1

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl ester

生成物 1

HCID 7045Quinoxaline収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To the solution of 2-9-2 (0.228 g, 0.745 mmol), (2S,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (0.219 g, 0.894 mmol) and Triphenylphosphine (0.293 g, 1.117 mmol) in THF (3.72 ml), the Diisopropyl azodicarboxylate (0.217 ml, 1.117 mmol) was added dropwise at room temperature. The mixture was stirred at room temperature for 2 h. The mixture was concentrated. The crude product was purified by combiflash (25 g silica gel, 0-40% ethyl acetate in Hexanes) to give 1-1-1 (0.320 g, 0.600 mmol, 81% yield). MS-ESI, m/z=534.45 (M+1)+.

後処理

  1. concentrationThe mixture was concentrated
  2. customThe crude product was purified by combiflash (25 g silica gel, 0-40% ethyl acetate in Hexanes)

出典と根拠

ORDレコード
ord-4f4ed4ac0bf84b4980af4c7408f0e16c
出典データセット
uspto-grants-2014_02
特許番号
US08648037B2

関連ノート

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