Diisopropylethylamine → HCID 59902310, compound

HRID 2230144Notes

Reaction equation

HRID 2230144 reaction equation
[OH:1][CH:2]([C:4]1([CH3:18])[CH2:8][NH:7][CH2:6][CH:5]1[C:9]1[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[C:13]([OH:15])[CH:14]=1)[CH3:3].CCN(C(C)C)C(C)C.[CH3:28][C:29]1([CH3:37])[O:33][C@H:32]([C:34](Cl)=[O:35])[CH2:31][O:30]1>C(Cl)Cl>[CH3:28][C:29]1([CH3:37])[O:33][C@@H:32]([C:34]([N:7]2[CH2:6][C@@H:5]([C:9]3[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[C:13]([OH:15])[CH:14]=3)[C@@:4]([C@H:2]([OH:1])[CH3:3])([CH3:18])[CH2:8]2)=[O:35])[CH2:31][O:30]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10374773HCID 10374773, compoundHCID 22246407HCID 22246407, compound

Product 1

HCID 59902310HCID 59902310, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A round bottom flask equipped with a stir bar and rubber septum was charged with 5-[4-(1-hydroxyethyl)-4-methylpyrrolidin-3-yl)-2-methoxyphenol (2.4 g, 9.55 mmol), dry CH2Cl2 (50 mls), and DIEA (3.49 mls, 20.1 mmol) under a nitrogen atmosphere. The mixture was chilled to 0° C. and (S)-2.2-dimethyl-[1,3]dioxolane-4-carbonyl chloride (3.14 g, 19.1 mmol) in 15 ml of CH2Cl2 was added dropwise by syringe. The reaction mixture was allowed to gradually warm to room temperature over a 16-hour period. The mixture then was diluted with 50 ml of CH2Cl2, washed with 1N HCl (2×50 ml), saturated aqueous NaHCO3 (1×50 ml), dried over Na2SO4, and concentrated to 3.9 g of a tan foam. The material was taken up in 100 ml CH3OH and chilled to 0° C. Three equivalents of aqueous 1N LiOH then were added (29 ml, 29.0 mmol), the mixture was stirred at 0° C. for 2 hours, then warmed to room temperature for 2 hours. The reaction mixture next was concentrated under reduced pressure with the bath temperature at 30° C. to remove CH3OH. The remaining aqueous material was neutralized with saturated NH4Cl to pH 7 and extracted with EtOAc (2×100 ml). The extracts were dried over Na2SO4, and concentrated to 2.74 g of a tan foam (76%).

Workup

  1. customA round bottom flask equipped with a stir bar
  2. temperatureto gradually warm to room temperature over a 16-hour period
  3. washwashed with 1N HCl (2×50 ml), saturated aqueous NaHCO3 (1×50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to 3.9 g of a tan foam
  6. temperaturechilled to 0° C
  7. additionThree equivalents of aqueous 1N LiOH then were added (29 ml, 29.0 mmol)
  8. temperaturewarmed to room temperature for 2 hours
  9. concentrationThe reaction mixture next was concentrated under reduced pressure with the bath temperature at 30° C.
  10. customto remove CH3OH
  11. extractionextracted with EtOAc (2×100 ml)
  12. dry with materialThe extracts were dried over Na2SO4
  13. concentrationconcentrated to 2.74 g of a tan foam (76%)

Sources & evidence

ORD record
ord-92b53f48e1784c0fb6d25ca0adac1992
Source dataset
uspto-grants-2002_07
Patent number
US06423710B1

Reaction notes

Loading…