HCID 54072221, compound → HCID 54175899, compound
Reaction equation
[CH2:1]([O:3][P:4]([CH:7]([N:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1)[P:8](=[O:11])([OH:10])[OH:9])(=[O:6])[OH:5])[CH3:2].[CH3:19][Mg]Br>O1CCCC1>[CH2:1]([O:3][P:4]([CH:7]([N:12]1[CH2:13][CH2:14][C:15]([OH:18])([CH3:19])[CH2:16][CH2:17]1)[P:8](=[O:9])([OH:10])[OH:11])(=[O:5])[OH:6])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
43 g (0.11 mol) of 4-oxopiperidinomethylene bisphosphonic acid ethyl ester was dissolved in 500 mt of dried tetrahydrofuran, and 250 ml (0.25 mol) of a methyl magnesium bromide solution in tetrahydrofuran (concentration: 1 mol/) was added thereto. The mixture was stirred at 25° C. for 2 hours, then subjected to post treatment and purified by column chromatography (SiO2, cyclohexane/CHCl3 =1/1) to give 30.7 g (68.5%) of 4-hydroxy-4-methylpiperidinomethylene bisphosphonic acid ethyl ester as an oily substance. To 15.8 g (39.5 mmol) of this ester, 7.6 g (47.2 mmol) of diethylaminosulfur trifluoride was added at -78° C. in CH2Cl2, and the mixture was stirred at room temperature for 5 hours. The reaction solution was purified by column chromatography (SiO2, hexane/isopropylether=5/1) to give 6.3 (40%) of the above identified compound.
Workup
- additionwas added
- custompurified by column chromatography (SiO2, cyclohexane/CHCl3 =1/1)
Sources & evidence
- ORD record
- ord-dad7476e6e64482abf7943f96b784e17
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05350743
Reaction notes
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