Reaction equation
[C:1]([CH2:3][CH2:4][O:5][P:6]([Cl:8])Cl)#[N:2].[CH:9]([NH:12][CH:13]([CH3:15])[CH3:14])([CH3:11])[CH3:10]>>[CH:9]([N:12]([CH:13]([CH3:15])[CH3:14])[P:6]([Cl:8])[O:5][CH2:4][CH2:3][C:1]#[N:2])([CH3:11])[CH3:10]Participants
Procedure
Chemistry FIG. 11 illustrates the synthesis of diphosphitylating and triphosphitylating reagents (6 and 7). Phosphorus trichloride (21, 20 mmol) was reacted with 3-hydroxypropionitrile (22, 1 eq) to yield 2-cyanoethylphosphorodichloridite (23). The subsequent reaction of 23 with diisopropylamine (20 mmol, 1 eq) afforded 2-cyanoethyl diisopropylphosphoramidochloridite (24). Addition of water (1 eq) gave the intermediate 25 that was reacted with 24 (1 eq) or 23 (0.5 eq) to yield the diphosphitylating (26, 97%) and triphosphitylating (27, 94%) reagents, respectively. The chemical structures of 26 and 27 were determined by nuclear magnetic resonance spectra (1H NMR, 13C NMR, 31P NMR) and high-resolution time of flight electrospray mass spectrometry. Stability studies using spectroscopic methods showed that the compounds remained stable even after two weeks storage at −20° C.
Sources & evidence
- ORD record
- ord-d0297b5a37b34c61858f44cfc6e2e5b0
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193384B2
Linked notes
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