Dimethyl Sulfide → 1-{[({(1R,2R)-2-[(4E)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-en-1-yl]cyclopropyl}oxy)carbonyl]oxy}pyrrolidine-2,5-dione

HRID 522358

反応式

HRID 522358 の反応式
C1CCCCC=1.CSC.[BH3:10].[CH2:11]([C@@H:16]1[CH2:18][C@H:17]1[O:19][C:20]([O:22][N:23]1[C:27](=[O:28])[CH2:26][CH2:25][C:24]1=[O:29])=[O:21])[CH2:12][CH2:13][C:14]#[CH:15].[B]1[O:34][C:33]([CH3:36])([CH3:35])[C:32]([CH3:38])([CH3:37])[O:31]1>C1COCC1.CCCCCCC>[CH3:37][C:32]1([CH3:38])[C:33]([CH3:36])([CH3:35])[O:34][B:10](/[CH:15]=[CH:14]/[CH2:13][CH2:12][CH2:11][C@@H:16]2[CH2:18][C@H:17]2[O:19][C:20]([O:22][N:23]2[C:27](=[O:28])[CH2:26][CH2:25][C:24]2=[O:29])=[O:21])[O:31]1

参加物

8

反応物 5

HCID 1068Dimethyl SulfideHCID 6331BoraneHCID 8079CyclohexeneHCID 6364989PinacolboraneHCID 895908351-[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)oxy]pyrrolidine-2,5-dione

生成物 1

HCID 895909291-{[({(1R,2R)-2-[(4E)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-en-1-yl]cyclopropyl}oxy)carbonyl]oxy}pyrrolidine-2,5-dione

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8900Heptane溶媒

実験手順

Cyclohexene (1.09 mL) was added to a 10 M dimethyl sulfide solution of borane (0.58 mL). Upon addition, a white solid had formed and 3 mL of degassed heptane was added to suspend it. The mixture was stirred for 5 minutes at room temperature. At this point, alkyne from Step 1 (15.5 g) in THF (55 mL) was added dropwise to the reaction mixture. After complete addition, the mixture was warmed to 40° C. for 20 minutes. Pinacolborane (8.48 mL) was added slowly to reaction mixture and the heating was continued for 2 hours at 40° C. The reaction mixture was cooled to room temperature and quenched with brine (100 mL). The mixture was extracted with ethyl acetate (3×). The combined organics were dried over magnesium sulfate, filtered and concentrated to provide the desired compound. 1H NMR (500 MHz, CDCl3): δ (ppm) 6.66-6.58 (m, 1H), 5.45 (d, 1H), 4.02-3.99 (m, 1H), 2.87 (s, 4H), 2.22-2.17 (m, 2H), 1.61-1.54 (m, 3H), 1.32-1.23 (m, 2H), 1.29 (s, 12H), 1.09-1.05 (m, 1H), 0.68-0.63 (m, 1H).

後処理

  1. additionUpon addition
  2. customa white solid had formed
  3. additionAfter complete addition
  4. temperaturethe mixture was warmed to 40° C. for 20 minutes
  5. waitthe heating was continued for 2 hours at 40° C
  6. temperatureThe reaction mixture was cooled to room temperature
  7. customquenched with brine (100 mL)
  8. extractionThe mixture was extracted with ethyl acetate (3×)
  9. dry with materialThe combined organics were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-d1d694d69f274a70aeb8a199894c7ab6
出典データセット
uspto-grants-2016_05
特許番号
US09328138B2

関連ノート

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