Methyl iodide → HCID 18997143, 화합물

HRID 1708049노트

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HRID 1708049 반응식
[CH:1](NC(C)C)(C)C.C([Li])CCC.[C:13]1([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.IC>C1COCC1>[C:13]1([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][C:24]([CH3:1])([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 18997131HCID 18997131, 화합물HCID 178418339Butyllithium

생성물 1

HCID 18997143HCID 18997143, 화합물수율 85.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To 2.64 mL (18.9 mmol) of diisopropylamine in 30 mL of dry THF at -78° was added 6.9 mL (17.3 mmol) of 2.5M n-butyllithium in hexanes. The mixture was allowed to warm to room temperature and then was cooled once again to -78°. To the stirred solution was added 4.11 g (15.7 mmol) of 1-(2-phenylethyl)-4-carboethoxypiperidine in 25 mL of dry THF. The mixture was allowed to warm to -40° and 0.98 mL (15.7 mmol) of iodomethane was added to the reaction mixture. The mixture was stirred at -40° for 15 minutes and then allowed to stir at room temperature for 3 hours. The mixture was evaporated to dryness and the residue was dissolved in water. The aqueous solution was extracted with methylene chloride and the extracts were dried and evaporated to give 3.70 g of 1-(2-phenylethyl)-4-methyl-4-carboethoxypiperidine as a yellow oil. NMR (CDCl3) δ7.15-7.21 (m, 5H); 4.11-4.20 (q, 4H); 2.71-2.94 (m, 4H): 2.52-2.61 (m, 2H): 2.11-2.24 (m, 4H); 1.47-1.59 (m, 2H); 1.21-1.30 (t, 3H); 1.20 (s, 3H).

후처리

  1. temperaturewas cooled once again to -78°
  2. temperatureto warm to -40°
  3. stirringto stir at room temperature for 3 hours
  4. customThe mixture was evaporated to dryness
  5. dissolutionthe residue was dissolved in water
  6. extractionThe aqueous solution was extracted with methylene chloride
  7. customthe extracts were dried
  8. customevaporated

출처 및 근거

ORD 기록
ord-112c55d4e8854576bfff811abf2a9951
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05356906

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