Triphenylphosphine → HCID 69007071, compound

HRID 1432049Notes

Reaction equation

HRID 1432049 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:48]([O:52][C:53]([C@@H:55]1[CH2:59][CH2:58][CH2:57][N:56]1[CH2:60][CH2:61]O)=[O:54])([CH3:51])([CH3:50])[CH3:49]>O1CCCC1.CCCCCCC>[C:48]([O:52][C:53]([C@@H:55]1[CH2:59][CH2:58][CH2:57][N:56]1[CH2:60][CH2:61][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)=[O:54])([CH3:51])([CH3:50])[CH3:49]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 690063851-(2-hydroxy-ethyl)-pyrrolidine-2-(S)-carboxylic acid tertbutyl esterHCID 69007907HCID 69007907, compound

Product 1

HCID 69007071HCID 69007071, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromo-2-(3-fluoro-phenylsulfanyl)-phenol (2.898 g, 9.69 mmol) and triphenylphosphine (3.558 g, 13.6 mmol) was dissolved in tetrahydrofuran (70 mL) and cooled to 0° C. under an inert atmosphere. To the solution was added DEAD (2.81 mL, 14.27 mmol)dropwise. After 25 minutes was added 1-(2-hydroxy-ethyl)-pyrrolidine-2-(S)-carboxylic acid tertbutyl ester (2.504 g, 1.163 mmol) in THF (15 mL) via cannulation. The mixture was stirred at room temperature for 16 hours. Heptane (350 mL) and THF (100 mL) was added. The organic phase was then washed with water (4×50 mL) and then brine, dried (Na2SO4), filtered and the filtrate concentrated in the presence of silica gel. The crude products absorbed onto silica gel and eluted with a gradient of heptane-heptane ethyl acetate (85:15). The product was isolated after concentration of relevant fractions.

Workup

  1. washThe organic phase was then washed with water (4×50 mL)
  2. dry with materialbrine, dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in the presence of silica gel
  5. customThe crude products absorbed onto silica gel
  6. washeluted with a gradient of heptane-heptane ethyl acetate (85:15)
  7. customThe product was isolated after concentration of relevant fractions

Sources & evidence

ORD record
ord-bf9429379aba41878fadbfb8ec00b6e7
Source dataset
uspto-grants-2009_11
Patent number
US07612068B2

Reaction notes

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