HCID 86752572, compound → HCID 86752571, compound

HRID 1290656Notes

Reaction equation

HRID 1290656 reaction equation
[CH2:1]([O:3][P:4]([C:9]1([P:19]([O:24][CH2:25][CH3:26])(=[O:23])[O:20][CH2:21][CH3:22])[CH:17]=[C:16]2[C:11]([CH:12]=[C:13](Br)[CH2:14][NH:15]2)=[CH:10]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C([Li])CCC>C1COCC1.CCCCCC>[CH2:21]([O:20][P:19]([C:9]1([P:4]([O:5][CH2:6][CH3:7])(=[O:8])[O:3][CH2:1][CH3:2])[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[N:15]2)=[CH:10]1)(=[O:23])[O:24][CH2:25][CH3:26])[CH3:22]

Participants

5

Reactant 2

HCID 86752572HCID 86752572, compoundHCID 178418339Butyllithium

Product 1

HCID 86752571HCID 86752571, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of dihydro-3-bromo-1-pyrindine-6,6-diphosphonic acid tetraethylester (10 mmol) in THF (10 ml) cooled to -78° C. is added a solution of n-butyllithium (2.1 equiv) in hexane over 30 minutes. The reaction is kept at -78° C. for an additional 30 minutes. To this solution is added 2-iodoethanol trimethylsilyl (TMS) ether (2.5 equiv) and the reaction is allowed to warm to room temperature over 30 minutes. After standard aqueous work-up, dihydro-3-(2-hydroxyethanol, TMS ether)-1-pyrindine-6,6-diphosphonic acid tetraethyl ester is isolated and used in the subsequent reaction without purification.

Sources & evidence

ORD record
ord-47129dd772464b70a3822a209141e8b9
Source dataset
uspto-grants-1998_05
Patent number
US05753634

Reaction notes

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