Tetrahydrofuran → 1-(Benzylamino)-1-(2-hydroxypropan-1-yl)cyclobutane

HRID 444779Notes

Reaction equation

HRID 444779 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([NH:15][C:16]1([CH:20](O)[CH2:21][CH3:22])[CH2:19][CH2:18][CH2:17]1)(=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1C[O:27]CC1>O.C(OCC)(=O)C>[CH2:7]([NH:15][C:16]1([CH2:20][CH:21]([OH:27])[CH3:22])[CH2:19][CH2:18][CH2:17]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 669353951-[1-(Benzoylamino)cyclobutyl]propanol

Product 1

HCID 581347701-(Benzylamino)-1-(2-hydroxypropan-1-yl)cyclobutaneYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8857Ethyl AcetateSolvent

Procedure

LiAlH4 (1.20 g, 31.6 mmol) was added to a solution of 1-[1-(benzoylamino) cyclobutyl]propanol (2.64 g, 11.3 mmol) in THF (40 mL) at room temperature. The mixture was stirred at room temperature for 1 hour and refluxed for 30 minutes. The mixture was cooled in an ice-water bath and a few drops of water were added. The mixture was then diluted with ethyl acetate, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (AcOEt) of the residue gave the title compound as a colorless oil (2.25 g, 91%). 1H-NMR (400 MHz, CDCl3) δ 1.21 (3H, d, J=6.1 Hz), 1.63 (1H, dd, J=13.7 and 2.4 Hz), 1.73-1.90 (5H, m), 2.04-2.13 (1H, m), 2.18-2.27 (1H, m), 3.59 (1H, d, J=11.6 Hz), 3.81 (1H, d, J=11.6 Hz), 4.07-4.16 (1H, m), 7.22-7.35 (5H, m).

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperatureThe mixture was cooled in an ice-water bath
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6db7805321db43efbd7369f2d6590d38
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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