Triphenylphosphine → HCID 59199400, compound

HRID 2089537Notes

Reaction equation

HRID 2089537 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:5]=[CH:4][C:3]1=2.[NH:20]1[CH:24]=[C:23]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[N:22]=[CH:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC)=O)=NC(OC)=O>C1COCC1.C(OCC)(=O)C>[CH:28]([O:27][C:25]([C:23]1[N:22]([CH:2]2[C:3]3[C:8](=[CH:7][C:6]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[CH:5][CH:4]=3)[CH2:9][CH2:10][CH2:11]2)[CH:21]=[N:20][CH:24]=1)=[O:26])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 351621Azodicarboxylic acid dimethyl esterHCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonateHCID 178459416HCID 178459416, compound

Product 1

HCID 59199400HCID 59199400, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of trifluoro-methanesulfonic acid 5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester (5.0 g, 0.016 mol) and isopropyl 4-imidazolecarboxylate, which can be prepared as described in Example 1 (1.72 g, 0.011 mol) in THF (100 mL) at 0° C. is added triphenylphosphine (4.20 g, 0.016 mol) and dimethyl azodicarboxylate (40% wt. in, toluene, 5.85 g, 0.016 mol). After 1 hour, the mixture is diluted with ethyl acetate and washed with water. The organic phase is dried with Na2SO4, filtered, and concentrated to give a residue, which is purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures) to give 3-(6-trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; 1H NMR (400 MHz, MeOD) δ ppm 1.37 (t, J=6.8 Hz, 6 H), 1.88-1.97 (m, 2 H), 2.27-2.34 (m, 2 H), 2.96 (dd, J=17.4, 6.3 Hz, 1 H), 3.11 (dd, J=17.4, 6.6 Hz, 1 H), 5.22 (t, J=6.8 Hz, 1 H), 6.36 (t, J=6.2 Hz, 1 H), 7.06 (d, J=8.8 Hz, 1 H), 7.19 (dd, J=8.8, 2.5 Hz, 1 H), 7.29 (d, J=2.5 Hz, 1 H), 7.58 (s, 1 H), 7.76 (d, J=1.0 Hz, 1 H).

Workup

  1. customcan be prepared
  2. washwashed with water
  3. dry with materialThe organic phase is dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue, which
  7. customis purified by silica gel chromatography (elution with hexanes-ethyl acetate mixtures)

Sources & evidence

ORD record
ord-bf6b612c8dcf4e2a93b34722f976768d
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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