Triphenylphosphine → Quinoxaline

HRID 240240

반응식

HRID 240240 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 7045Quinoxaline수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-4f4ed4ac0bf84b4980af4c7408f0e16c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648037B2

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