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Triphenylphosphine → HCID 69006959, compound

HRID 1432047
Notes
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Reaction equation

HRID 1432047 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:9])=[C:6]([OH:8])[CH:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:43]([O:47][C:48]([C@@H:50]1[CH2:54][CH2:53][CH2:52][N:51]1[CH2:55][CH2:56]O)=[O:49])([CH3:46])([CH3:45])[CH3:44]>C1COCC1>[C:43]([O:47][C:48]([C@@H:50]1[CH2:54][CH2:53][CH2:52][N:51]1[CH2:55][CH2:56][O:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[I:9])=[O:49])([CH3:46])([CH3:45])[CH3:44]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 66133335-Chloro-2-iodophenolHCID 690063851-(2-hydroxy-ethyl)-pyrrolidine-2-(S)-carboxylic acid tertbutyl ester

Product 1

HCID 69006959HCID 69006959, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

5-Chloro-2-iodophenol (801 mg, 3.15 mmol) and PPh3 (1.15 g, 4.41 mmol) were dissolved in THF (25 mL). DIAD (0.91 mL, 4.62 mmol). was added dropwise and the solution was stirred for 20 min. A solution of 1-(2-hydroxy-ethyl)-pyrrolidine-2-(S)-carboxylic acid tert butyl ester (816 mg, 3.79 mmol) in THF (4 mL) was added via canulation. The mixture was stirred for 40 min at 0° C. then for 1.5 h at room temperature and finally for 3 h at 50° C. The mixture was diluted with heptanes (100 mL), washed with water (4×25 mL), dried over Na2SO4 and evaporated onto silica gel. After flash chromatography using silica gel, eluting with heptanes/EtOAc, 9:1, the title compound was obtained as a colorless oil (1.023 g, 72%).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred for 40 min at 0° C.
  3. waitfor 1.5 h at room temperature
  4. waitfinally for 3 h at 50° C
  5. washwashed with water (4×25 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated onto silica gel
  8. washeluting with heptanes/EtOAc, 9:1

Sources & evidence

ORD record
ord-1e77f6fb2dd3418984eac637e48d6d6f
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07612068B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes