Sodium Hydroxide → HCID 178482718, compound

HRID 1159356Notes

Reaction equation

HRID 1159356 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].N1(CC2C=CC(O)=CC=2)CCCC1.[CH2:20]([N:27]([CH3:35])[C:28]([CH:30]1[CH2:33][C:32](=[O:34])[CH2:31]1)=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>C1COCC1.O>[CH2:20]([N:27]([CH2:28][C@@H:30]1[CH2:31][C@H:32]([OH:34])[CH2:33]1)[CH3:35])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 187719784-(Pyrrolidin-1-ylmethyl)phenolHCID 21226445Aluminium lithium hydrideHCID 68619645HCID 68619645, compound

Product 1

HCID 178482718HCID 178482718, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (5.4 g, 0.14 mol) was added to a solution of intermediate 2, N-Benzyl-N-methyl-3-oxocyclobutanecarboxamide (15.5 g, 0.07 mol) in absolute THF (100 mL) under stirring in argon. The mixture was refluxed under stirring for 2 h and cooled. Then 10 N NaOH (14 mL) and water (5 mL) were added. The organic layer was decanted, and the aqueous one was extracted with THF (2×50 mL). The organic layers were evaporated to afford the title compound (8.6 g, 59%) as a colorless oil. 1H NMR-data (DMSO-d6): 7.19-7.33 (m, 5H, Ph); 4.85 (d, 1H, OH, J=6.6); 3.83-3.94 (m, 1H); 3.40 (s, 2H, CH2); 2.24-2.34 (m, 4H); 2.07 (s, 3H, NCH3); 1.81-1.92 (m, 1H); 1.34-1.44 (m, 2H).

Workup

  1. temperatureThe mixture was refluxed
  2. stirringunder stirring for 2 h
  3. temperaturecooled
  4. customThe organic layer was decanted
  5. extractionthe aqueous one was extracted with THF (2×50 mL)
  6. customThe organic layers were evaporated

Sources & evidence

ORD record
ord-8fa0a111acd34b4789c2b581e62cacd5
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

Loading…