Triphenylphosphine → Quinoxaline

HRID 240240

Reaction equation

HRID 240240 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 7045QuinoxalineYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-4f4ed4ac0bf84b4980af4c7408f0e16c
Source dataset
uspto-grants-2014_02
Patent number
US08648037B2

Linked notes

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