Water → HCID 178521632, compound

HRID 1159390Notes

Reaction equation

HRID 1159390 reaction equation
[CH2:1]([NH:8][C:9]([CH:11]1[CH2:14][C:13](=[O:15])[CH2:12]1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].O>C1COCC1>[CH2:1]([NH:8][CH2:9][C@@H:11]1[CH2:14][C@H:13]([OH:15])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68619384N-Benzyl-3-oxocyclobutanecarboxamide

Product 1

HCID 178521632HCID 178521632, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of intermediate 26 N-Benzyl-3-oxocyclobutanecarboxamide (9.5 g, 0.046 mol) in absolute THF (50 mL) was added to a suspension of LiAlH4 (3.55 g, 0.093 mol) in absolute THF (50 ml) under stirring in argon. The mixture was refluxed under stirring for 1 h and cooled. Then 10 N NaOH (10 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 give the title compound (7.4 g, 83%) as a yellow oil. 1H NMR-data (DMSO-d6): 7.00-7.49 (m, 6H, NH, Ph); 4.80 (br.s, 1H, OH); 3.81-3.95 (m, 1H); 3.67 (s, 2H, CH2); 2.48 (d, 2H, CH2, J=6.8 Hz); 2.19-2.30 (m, 2H); 1.70-1.84 (m, 1H); 1.35-1.50 (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

Sources & evidence

ORD record
ord-3866b73a96074495925a24aabadaea81
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

Loading…