Water → HCID 58134854, compound

HRID 444786Notes

Reaction equation

HRID 444786 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([NH:15][C:16]1([CH2:20][C:21]([NH2:23])=O)[CH2:19][CH2:18][CH2:17]1)(=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>C1COCC1>[CH2:7]([NH:15][C:16]1([CH2:20][CH2:21][NH2:23])[CH2:19][CH2:18][CH2:17]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 58134864HCID 58134864, compound

Product 1

HCID 58134854HCID 58134854, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAlH4 (570 mg, 15.0 mmol) was added portionwise to a solution of [1-(benzoylamino) cyclobutyl]acetamide (687 mg, 3.00 mmol) in THF (30 mL) at room temperature over the course of 30 minutes, and the mixture was heated to reflux for 5 hours. The mixture was cooled in an ice-water bath, aqueous THF and few drops of water were added, and the mixture was allowed to stand overnight. The mixture was filtered through celite and the solution was dried over anhydrous Na2SO4. The solution was concentrated in vacuo to give the title compound as a pale yellow oil (609 mg, 99%). 1H-NMR (400 MHz, CDCl3) δ 1.65-1.80 (2H, m), 1.82 (2H, t, J=7.3 Hz), 1.86-2.02 (4H, m), 2.82 (2H, t, J=7.3 Hz), 3.65 (2H, s), 7.20-7.38 (5H, m).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hours
  3. temperatureThe mixture was cooled in an ice-water bath
  4. filtrationThe mixture was filtered through celite
  5. dry with materialthe solution was dried over anhydrous Na2SO4
  6. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-390fa0f6a07945339cfa37df22b6dd37
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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