Ammonium Chloride → HCID 58134705, compound

HRID 444778Notes

Reaction equation

HRID 444778 reaction equation
[CH3:1][Mg]Cl.[C:4]([NH:12][C:13]1([CH2:17][CH:18]=[O:19])[CH2:16][CH2:15][CH2:14]1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH4+].[Cl-]>C1COCC1>[C:4]([NH:12][C:13]1([CH2:17][CH:18]([OH:19])[CH3:1])[CH2:16][CH2:15][CH2:14]1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 58134729HCID 58134729, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 58134705HCID 58134705, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl magnesium chloride (14.0 mL, 3M solution in THF) was added to a stirred solution of [1-(benzoylamino)cyclobutyl]acetaldehyde (2.82 g, 13.0 mmol) in THF (30 mL) at −0° C., and the mixture was stirred at room temperature for 5 hours. Saturated aqueous NH4Cl (10 mL) was added to the mixture 0° C., and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were 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 oil (2.65 g, 87%). 1H-NMR (400 MHz, CDCl3) δ 1.25 (3H, d, J=6.1 Hz), 1.77-2.12 (5H, m), 2.28-2.40 (1H, m), 2.52 (1H, q, J=10.4 Hz), 2.75-2.85 (1H, m), 3.26 (1H, d, J=3.7 Hz), 3.97-4.07 (1H, m), 6.91 (1H, brs), 7.39-7.46 (2H, m), 7.46-7.53 (1H, m), 7.75-7.82 (2H, m).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ac3563aaed544d2b44cec2994badf21
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

Loading…