Triphenylphosphine → HCID 17756287, compound

HRID 888077Notes

Reaction equation

HRID 888077 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:14])([F:13])[F:12])=[C:8]([OH:10])[CH:9]=1)([O-:3])=[O:2].[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@@H:23]1[CH2:27]O)=[O:21])([CH3:18])([CH3:17])[CH3:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:11]([F:12])([F:13])[F:14])=[C:8]([CH:9]=1)[O:10][CH2:27][C@H:23]1[CH2:24][CH2:25][CH2:26][N:22]1[C:20]([O:19][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:21])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 688279N-(tert-Butoxycarbonyl)-D-prolinolHCID 5462977Diethyl azodicarboxylateHCID 219595865-Nitro-2-(trifluoromethyl)phenol

Product 1

HCID 17756287HCID 17756287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-nitro-2-trifluoromethylphenol (2.83 g, 13.7 mmol), (R)-(+)-(tert-butoxy-carbonyl)-2-pyrrolidinemethanol (2.75 g, 13.7 mmol), and PPh3 (3.58 g, 13.7 mmol) in 24 mL THF, cooled at −20° C. was added dropwise over 1.5 h a 12 mL THF solution containing DEAD (2.43 g, 13.9 mmol). The mixture turned a deep red. The reaction was warmed gradually to RT and stirred for 18 h. The reaction was concentrated in vacuo and treated with a small mixture of hexanes and Et2O. After sonication, the solids were filtered off, and the filtrate was concentrated in vacuo. The crude was dissolved in a very small amount of EtOAc and Et2O then diluted with hexanes, which were washed once with 0.1N HCl, 3 times with 2N NaOH, and once with brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography using 5% EtOAc in hexanes to yield the title compound as a clear thick oil.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiontreated with a small mixture of hexanes and Et2O
  3. customAfter sonication
  4. filtrationthe solids were filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe crude was dissolved in a very small amount of EtOAc and Et2O
  7. additionthen diluted with hexanes, which
  8. washwere washed once with 0.1N HCl, 3 times with 2N NaOH
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-12e2c421e4c24f2cb07d14b851733d3e
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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