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

HRID 2176956Notes

Reaction equation

HRID 2176956 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-be325cd766ec4b4095c34b278be9a385
Source dataset
uspto-grants-2015_06
Patent number
US09067882B2

Reaction notes

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