N,3,3-Trimethoxy-N-methylcyclobutanecarboxamide → HCID 89527308, compound

HRID 1778565Notes

Reaction equation

HRID 1778565 reaction equation
CON(C)[C:4]([CH:6]1[CH2:9][C:8]([O:12][CH3:13])([O:10][CH3:11])[CH2:7]1)=[O:5].[CH2:15]([Mg]Br)[CH2:16][CH:17]=[CH2:18]>C1COCC1>[CH3:13][O:12][C:8]1([O:10][CH3:11])[CH2:7][CH:6]([C:4](=[O:5])[CH2:18][CH2:17][CH:16]=[CH2:15])[CH2:9]1

Participants

4

Reactant 2

HCID 86624599N,3,3-Trimethoxy-N-methylcyclobutanecarboxamideHCID 178418797HCID 178418797, compound

Product 1

HCID 89527308HCID 89527308, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N,3,3-trimethoxy-N-methylcyclobutanecarboxamide (12.19 g, 60.0 mmol) was dissolved in THF (130 mL), cooled to 0° C. and treated with 3-butenylmagnesium bromide (168 mL, 0.5 M/THF, 84 mmol). After stirring for 1.5 h at room temperature, the reaction was re-cooled to 0° C. and quenched with 1 N citric acid (30 mL), diluted with ethyl acetate, washed successively with water, saturated aqueous sodium chloride, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5-40% ethyl acetate in heptane to afford the desired product 10.98 g (92%). Rf 0.77 (50% ethyl acetate in heptane). 1H NMR (CDCl3, 300 MHz) δ 5.87-5.72 (m, 1H), 5.06-4.95 (m, 2H), 3.17 (s, 3H), 3.13 (s, 3H), 3.06-2.88 (m, 1H), 2.54-2.48 (m, 2H), 2.38-2.28 (m, 6H).

Workup

  1. temperaturethe reaction was re-cooled to 0° C.
  2. customquenched with 1 N citric acid (30 mL)
  3. additiondiluted with ethyl acetate
  4. washwashed successively with water, saturated aqueous sodium chloride
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with 5-40% ethyl acetate in heptane

Sources & evidence

ORD record
ord-6c7c5e41cae946c687731d94d7ff0043
Source dataset
uspto-grants-2016_02
Patent number
US09266908B2

Reaction notes

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