Triphenylphosphine → HCID 54162185, compound

HRID 1358947Notes

Reaction equation

HRID 1358947 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].[CH3:13][N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:13][N:14]1[CH2:18][CH2:17][CH2:16][C@@H:15]1[O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 694712-Methoxy-5-nitrophenolHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 54162185HCID 54162185, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methoxy-5-nitrophenol (5.58 g; 0.033 mol), (S)-1-methyl-2-hydroxymethylpyrrolidine (3.45 g; 0.03 mol) and triphenylphosphine (8.65 g; 0.033 mol) in dry THF (80 ml) was cooled to 50 and treated with DEAD (5.2 ml; 0.033 mol) over 15 min. The reaction mixture was allowed to stand at RT for 16 h, then evaporated in vacuo and partitioned 5% NaOH(aq)/Et2O. The organic phase was separated and extracted with 10% HCl(aq). The aqueous extract was washed with Et2O, basified with 40% NaOH(aq) and extracted with Et2O. The organic extracts were washed with H2O, dried over Na2SO4 and evaporated in vacuo to yield the title compound (D43) (6.79 g; 85%) MH+=267.

Workup

  1. customevaporated in vacuo
  2. custompartitioned 5% NaOH(aq)/Et2O
  3. customThe organic phase was separated
  4. extractionextracted with 10% HCl(aq)
  5. extractionThe aqueous extract
  6. washwas washed with Et2O
  7. extractionextracted with Et2O
  8. washThe organic extracts were washed with H2O
  9. dry with materialdried over Na2SO4
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-3d83b50842d54e7da62185f25ae8c249
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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