Potassium Carbonate → Cis-1-Methyl-3-[(9Z,12Z)-Octadeca-9,12-Dien-1-Yloxy]-4-(Octyloxy)Pyrrolidine

HRID 2176956ノート

反応式

HRID 2176956 の反応式
[CH2:1]([O:19][CH:20]1[CH:24]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:23][N:22]([C:34](OCC2C=CC=CC=2)=O)[CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O-])([O-])=O.[K+].[K+].CC(OC)(C)C>C1COCC1>[CH3:34][N:22]1[CH2:23][C@H:24]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C@H:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:21]1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 21226445Aluminium lithium hydrideHCID 86694890Benzyl 3-[(9Z,12Z)-Octadeca-9,12-Dien-1-Yloxy]-4-(Octyloxy)Pyrrolidine-1-Carboxylate

生成物 1

HCID 86694891Cis-1-Methyl-3-[(9Z,12Z)-Octadeca-9,12-Dien-1-Yloxy]-4-(Octyloxy)Pyrrolidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In a 100 mL RBF fitted with reflux condenser, compound 10 (4 g, 6.69 mmol) was dissolved in 26 mL THF for addition of the lithium aluminum hydride (13.38 ml, 13.38 mmol). Heated to reflux in a 85 C. oil bath. After 2 h, HPLC shows complete dissappearance of the SM. Cooled to RT and poured into 200 mL IM K2CO3 and 200 mL MTBE. Stirred for 30 min, separated layers and then extracted with 100 mL MTBE. Dried combined organics over Na2SO4, filtered through Celite and concentrated. Flash chromatography (10-30% IPA in DCM) provided compound 11 as a clear oil. 1H NMR (400 MHz, CDCl3) δ 5.39 (m, 4H), 3.93 (m, 2H), 3.50 (m, 4H), 3.04 (m, 2H), 2.79 (m, 2H), 2.48 (m, 2H), 2.39 (s, 3H), 2.08 (m, 4H), 1.62 (m, 4H), 1.40-1.25 (m, 26H), 0.91 (m, 6H).

後処理

  1. customIn a 100 mL RBF fitted
  2. temperaturewith reflux condenser
  3. temperatureHeated
  4. temperatureto reflux in a 85 C
  5. customseparated layers
  6. extractionextracted with 100 mL MTBE
  7. customDried
  8. filtrationfiltered through Celite
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-be325cd766ec4b4095c34b278be9a385
出典データセット
uspto-grants-2015_06
特許番号
US09067882B2

反応ノート

読み込み中…