HCID 86752572, compound → HCID 86752571, compound

HRID 963643Notes

Reaction equation

Br[C:2]1[CH2:3][NH:4][C:5]2[C:9]([CH:10]=1)=[CH:8][C:7]([P:19]([O:24][CH2:25][CH3:26])(=[O:23])[O:20][CH2:21][CH3:22])([P:11]([O:16][CH2:17][CH3:18])(=[O:15])[O:12][CH2:13][CH3:14])[CH:6]=2.C([Li])CCC>C1COCC1.CCCCCC>[N:4]1[C:5]2[C:9](=[CH:8][C:7]([P:19]([O:24][CH2:25][CH3:26])(=[O:23])[O:20][CH2:21][CH3:22])([P:11]([O:12][CH2:13][CH3:14])(=[O:15])[O:16][CH2:17][CH3:18])[CH:6]=2)[CH:10]=[CH:2][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of dihydro-3-bromo-1-pyrindine-6,6-bisphosphonic acid, tetraethyl ester (10 mmol) [prepared as described in Example E (part I) hereinbefore] in THF (10 ml) cooled to -78° C. is added a solution of n-butyllithium (2.1 equivalent) in hexane over 30 minutes. The reaction is kept at -78° C. for an additional 30 minutes. To this solution is added 4-iodobutanol trimethylsilyl (TMS) ether (2.5 equivalent) and the reaction is allowed to warm to room temperature over 30 minutes. After standard aqueous work-up, dihydro-3-(4-butanol, TMS ether)-1-pyrindine-6,6-bisphosphonic acid, tetraethyl ester is isolated and used in the next reaction without purification.

Workup

temperatureto warm to room temperature over 30 minutes

Sources & evidence

ORD record: ord-a96824d03ee64cd180410b173bc7f59b
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763611

Reaction notes

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