Methanol → HCID 66935184, compound

HRID 1396103Notes

Reaction equation

HRID 1396103 reaction equation
CC(C[AlH]CC(C)C)C.[C:10]([NH:18][C:19]1([CH2:23][C:24](OCC)=O)[CH2:22][CH2:21][CH2:20]1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[OH:30].[NH4+].[Cl-]>C1COCC1>[C:10]([NH:18][C:19]1([C:23](=[O:30])[CH3:24])[CH2:22][CH2:21][CH2:20]1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 58134741HCID 58134741, compound

Product 1

HCID 66935184HCID 66935184, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

DIBAL (40.0 mL, 1M solution in toluene) was added dropwise at −78° C. to a stirred solution of ethyl [1-(benzoylamino)cyclobutyl]acetate (6.86 g, 26.3 mmol) in THF (130 mL) over the course of 30 minutes. After stirring at −78° C. for 6 hours, MeOH (10 mL) was added dropwise to the mixture at −78° C. over the course of 30 minutes. Saturated aqueous NH4Cl (20 mL) was then added to the mixture, and the mixture was stirred at room temperature for 1 hour. The mixture was extracted with Et2O, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (hexane:AcOEt=2:1) of the residue gave the title compound as a colorless solid (1.82 g, 32%). 1H-NMR (400 MHz, CDCl3) δ 1.87-2.07 (2H, m), 2.25-2.34 (2H, m), 2.36-2.45 (2H, m), 3.28 (2H, s), 6.57 (1H, brs), 7.39-7.45 (2H, m), 7.46-7.53 (1H, m), 7.70-7.76 (2H, m), 9.79 (1H, s).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionThe mixture was extracted with Et2O
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93bbba596aca42a4a5df3772fc591f71
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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