Triphenylphosphine → Quinoxaline

HRID 1506611Notes

Reaction equation

HRID 1506611 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-592c81e3ea9745bbb1d01cf487c40a5c
Source dataset
uspto-grants-2015_12
Patent number
US09220748B2

Reaction notes

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