Tetrahydrofuran → [2-(4-Oxo-1-(tosyl)-1,2,3,4-tetrahydroquinolin-3-yl)ethylidene]bisphosphonic acid tetraethyl ester

HRID 36158Notes

Reaction equation

HRID 36158 reaction equation
[S:1]([N:11]1[CH2:20][C:19](=O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:22]([O:24][P:25]([C:30]([P:32](=[O:39])([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35])=[CH2:31])(=[O:29])[O:26][CH2:27][CH3:28])[CH3:23].C1CCN2C(=NCCC2)CC1.C1C[O:54]CC1>C(OCC)(=O)C>[CH2:37]([O:36][P:32]([CH:30]([P:25](=[O:29])([O:26][CH2:27][CH3:28])[O:24][CH2:22][CH3:23])[CH2:31][CH:19]1[C:18](=[O:54])[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:11]([S:1]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=2)(=[O:3])=[O:2])[CH2:20]1)(=[O:39])[O:33][CH2:34][CH3:35])[CH3:38]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5896332-tosyl-2,3-dihydroisoquinolin-4(1H)-oneHCID 11022954Tetraethyl vinylidene phosphonate

Product 1

HCID 86748669[2-(4-Oxo-1-(tosyl)-1,2,3,4-tetrahydroquinolin-3-yl)ethylidene]bisphosphonic acid tetraethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The ketone (II, 4.27 g), ethenylidenebisphosphonic acid tetraethyl ester (I, 3.60 g) and DBU (2 ml) are stirred in THF (30 ml) for 1 hour. The reaction is diluted with ethyl acetate, washed with hydrochloric acid (IN), saturated sodium bicarbonate, and saline, dried with magnesium sulfate, and concentrated under reduced pressure. The product is chromatographed eluting with ethyl acetate/ethyl acetate-acetone 1/1) to give the title compound, MS (m/e) 601, 446, 400, 372 and 155; IR (neat) 2983, 1689, 1599, 1574, 1494, 1477, 1392 and 1254 cm-1 ; NMR (CDCl3) 7.95, 7.8, 7.7, 7.49, 7.28, 7.14, 4.47, 4.20, 3.79, 3.14, 2.83, 2.4, 1.93 and 1.32 δ.

Workup

  1. washwashed with hydrochloric acid (IN), saturated sodium bicarbonate, and saline
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe product is chromatographed
  5. washeluting with ethyl acetate/ethyl acetate-acetone 1/1)

Sources & evidence

ORD record
ord-287f4dad955d4b93a760335c4d894385
Source dataset
uspto-grants-1995_05
Patent number
US05412141

Reaction notes

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