Sodium Hydroxide → HCID 178521632, compound

HRID 1159361Notes

Reaction equation

HRID 1159361 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].O[C@@H]1C[C@H](CN(C)C(=O)OC(C)(C)C)C1.[CH2:22]([NH:29][C:30]([CH:32]1[CH2:35][C:34](=[O:36])[CH2:33]1)=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+]>C1COCC1.O>[CH2:22]([NH:29][CH2:30][C@@H:32]1[CH2:35][C@H:34]([OH:36])[CH2:33]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68619384N-Benzyl-3-oxocyclobutanecarboxamideHCID 178484138HCID 178484138, compound

Product 1

HCID 178521632HCID 178521632, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (2.7 g, 0.07 mol) was added to a solution of intermediate 7, N-Benzyl-3-oxocyclobutanecarboxamide (7.12 g, 0.035 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 (2 mL) and water (1 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 (3.9 g, 58%) as a colorless 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 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-47cdbc247c4e42d2b76fb6d56a90975b
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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