N,N,N',N'-Tetramethylethylenediamine → HCID 69264112, compound

HRID 1593014Notes

Reaction equation

HRID 1593014 reaction equation
CN(C)CCN(C)C.[C:9]1([Mg]Br)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O-]S(C(F)(F)F)(=O)=O.C([B+]CCCC)CCC.[CH3:34][S:35]([C:38]1[CH:43]=[CH:42][C:41](/[CH:44]=[CH:45]/[C:46]([N:48]2[C@H:52]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C@H:51]([CH3:59])[N:50]([CH3:60])[C:49]2=[O:61])=[O:47])=[CH:40][CH:39]=1)(=[O:37])=[O:36]>C1COCC1.[Cu]I>[CH3:34][S:35]([C:38]1[CH:39]=[CH:40][C:41]([C@H:44]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:45][C:46]([N:48]2[C@H:52]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C@H:51]([CH3:59])[N:50]([CH3:60])[C:49]2=[O:61])=[O:47])=[CH:42][CH:43]=1)(=[O:36])=[O:37]

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 69238885HCID 69238885, compoundHCID 178418255HCID 178418255, compoundHCID 178418657HCID 178418657, compound

Product 1

HCID 69264112HCID 69264112, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of copper (I) iodide (960 mg, 5.0 mmol) and THF (20 mL) was added N,N,N′,N′-tetramethylethylenediamine (0.83 mL, 5.5 mmol) and the resulting mixture was stirred at room temperature for 10 min. then cooled to −78° C. Phenylmagnesium bromide (5.0 mL, 1M in THF, 5.0 mmol) was added and the resulting mixture stirred at −78° C. for 15 min. A solution of di-n-butylboron triflate (3.0 mL, 1M in diethyl ether, 3.0 mmol) and (E)-(4S,5R)-1-(3-[4-methanesulfonylphenyl]acryloyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one (Method D, 1.0 g, 2.51 mmol) in THF (15 mL) was added and the resulting mixture was stirred whilst allowing to warm to room temperature for 18 h. The reaction mixture was washed with saturated aqueous ammonium chloride, water and brine, dried (MgSO4) and evaporated. The residue was purified by eluting through a 20 g Bond Elut with gradient of isohexane to ethyl acetate giving the sub-titled compound (1.49 g, 100%); NMR (CDCl3): 0.78 (d, 3H), 2.82 (s, 3H), 3.00 (s, 3H), 3.78 (dd, 1H), 3.80 (m, 1H), 3.98 (dd, 1H), 4.72 (m, 1H), 5.19 (d, 1H), 6.99 (m, 2H), 7.22 (m, 8H), 7.48 (d, 2H), 7.79 (d, 2H); MS: 477 (MH+).

Workup

  1. temperaturethen cooled to −78° C
  2. stirringthe resulting mixture stirred at −78° C. for 15 min
  3. stirringthe resulting mixture was stirred
  4. temperatureto warm to room temperature for 18 h
  5. washThe reaction mixture was washed with saturated aqueous ammonium chloride, water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified
  9. washby eluting through a 20 g Bond Elut with gradient of isohexane to ethyl acetate giving the sub-titled compound (1.49 g, 100%)

Sources & evidence

ORD record
ord-d9aa373b8dd843ceb872890c7551b714
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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