Sodium Hydroxide → HCID 178482718, compound

HRID 1159367Notes

Reaction equation

HRID 1159367 reaction equation
CN(CC1CC(OC2C=CC(CN3CCCC3)=CC=2)C1)S(CC(F)(F)F)(=O)=O.[CH2:29]([N:36]([CH3:44])[C:37]([CH:39]1[CH2:42][C:41](=[O:43])[CH2:40]1)=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1.O>[CH2:29]([N:36]([CH2:37][C@@H:39]1[CH2:40][C@H:41]([OH:43])[CH2:42]1)[CH3:44])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68619023HCID 68619023, compoundHCID 68619645HCID 68619645, compound

Product 1

HCID 178482718HCID 178482718, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of intermediate 2, N-benzyl-N-methyl-3-oxocyclobutanecarboxamide (27.9 g, 0.128 mol) in absolute THF (40 mL) was added to a suspension of LiAlH4 (9.75 g, 0.257 mol) in absolute THF (200 ml) under stirring in argon. The mixture was refluxed under stirring for 1 h and cooled. Then 10 N NaOH (25 mL) and water (25 mL) were added. The organic layer was decanted, and the aqueous one was extracted with THF (2×50 mL). The organic layers were evaporated. The residue was purified by chromatography (silica gel, 63-100 μm, 300 g, CHCl3/MeOH 100:0→90:10). The title compound (25 g, 95%) was obtained as a colorless oil. 1H NMR-data (DMSO-d6): 7.19-7.33 (m, 5H, Ph); 4.85 (d, 1H, OH, J=6.6 Hz); 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 1 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
  7. customThe residue was purified by chromatography (silica gel, 63-100 μm, 300 g, CHCl3/MeOH 100:0→90:10)

Sources & evidence

ORD record
ord-811186c9800b44b49ac4b482b84f8cb1
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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