Triphenylphosphine → HCID 69006959, compound
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]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- additionwas added dropwise
- stirringThe mixture was stirred for 40 min at 0° C.
- waitfor 1.5 h at room temperature
- waitfinally for 3 h at 50° C
- washwashed with water (4×25 mL)
- dry with materialdried over Na2SO4
- customevaporated onto silica gel
- washeluting with heptanes/EtOAc, 9:1
Sources & evidence
- ORD record
- ord-1e77f6fb2dd3418984eac637e48d6d6f
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612068B2
Reaction notes
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