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

HRID 1593014노트

반응식

HRID 1593014 반응식
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]

참가 물질

7

반응물 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 69238885HCID 69238885, 화합물HCID 178418255HCID 178418255, 화합물HCID 178418657HCID 178418657, 화합물

생성물 1

HCID 69264112HCID 69264112, 화합물

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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+).

후처리

  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%)

출처 및 근거

ORD 기록
ord-d9aa373b8dd843ceb872890c7551b714
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07294636B2

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