Iodine → 1-Benzyl-4-(2-methyl-pentyl)-pyrrolidin-2-one

HRID 130520

반응식

HRID 130520 반응식
[Mg].II.Br[CH:5]([CH2:7][CH2:8][CH3:9])[CH3:6].[CH2:10]([N:17]1[CH2:21][CH:20]([CH2:22]I)[CH2:19][C:18]1=[O:24])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([N:17]1[CH2:21][CH:20]([CH2:22][CH:5]([CH3:6])[CH2:7][CH2:8][CH3:9])[CH2:19][C:18]1=[O:24])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 78902-BromopentaneHCID 5462224MagnesiumHCID 128272761-Benzyl-4-iodomethyl-pyrrolidin-2-one

생성물 1

HCID 218882331-Benzyl-4-(2-methyl-pentyl)-pyrrolidin-2-one수율 69%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of magnesium turnings (0.50 g, 0.021 mol) in 15 mL of dry THF under nitrogen, was added an iodine crystal and 2-bromopentane (2.88 g, 0.019 mol). After an exothermic reaction which was periodically cooled in an ice bath, the reaction was stirred at room temperature for 2 hours. Eight milliliters of Li2CuCl4 (made from 84 mg LiCl and 134 mg CuCl2 in 10 mL of dry THF) was added at 0° C. followed by dropwise addition of 1-Benzyl-4-iodomethyl-pyrolidine-2-one 75 in 15 mL dry THF, and the resulting suspension was let stir at 0° C. for 3 hours. Stirring was continued at room temperature for 1 hour before quenching with a saturated solution of ammonium chloride. Water was added to dissolve the precipitate formed, and the solution was then extracted with ether and dried over magnesium sulfate. The solvent was evaporated under vacuum and the residue chromatographed on silica eluting with 1:1 acetone/hexane to give 1.13 g, 69% of the 1-benzyl-4-(2-methyl-pentyl)-pyrrolidin-2-one 76. 1H NMR (CDCl3) δ 7.30 (m, 5H), 4.44 (m, 2H), 3.32 (m, 1H), 2.86 (m, 1H), 2.56 (m, 1H), 2.40 (m, 1H), 2.10 (m, 1H), 1.30 (m, 6H), 1.10 (m, 1H), 0.90 (m, 6H). MS, m/z (relative intensity): 261 [M+2H, 100%], 301 [M−H+CH3CN, 82%], 260 [M+H, 72%].

후처리

  1. customAfter an exothermic reaction which
  2. temperaturewas periodically cooled in an ice bath
  3. stirringthe resulting suspension was let stir at 0° C. for 3 hours
  4. stirringStirring
  5. waitwas continued at room temperature for 1 hour
  6. custombefore quenching with a saturated solution of ammonium chloride
  7. additionWater was added
  8. dissolutionto dissolve the precipitate
  9. customformed
  10. extractionthe solution was then extracted with ether
  11. dry with materialdried over magnesium sulfate
  12. customThe solvent was evaporated under vacuum
  13. customthe residue chromatographed on silica eluting with 1:1 acetone/hexane

출처 및 근거

ORD 기록
ord-d63168ab4abf447d88c381d7be11c418
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381747B2

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