N,N,N',N'-Tetramethylethylenediamine → HCID 69264112、化合物

HRID 1593014ノート

反応式

HRID 1593014 の反応式
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]

参加物

7

反応物 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 69238885HCID 69238885、化合物HCID 178418255HCID 178418255、化合物HCID 178418657HCID 178418657、化合物

生成物 1

HCID 69264112HCID 69264112、化合物

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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+).

後処理

  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%)

出典と根拠

ORDレコード
ord-d9aa373b8dd843ceb872890c7551b714
出典データセット
uspto-grants-2007_11
特許番号
US07294636B2

反応ノート

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