HCID 86696501, compound → HCID 1490683, compound

HRID 1615902Notes

Reaction equation

HRID 1615902 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:13][C@@H:12]2[C:14](N(OC)C)=[O:15])=[CH:7][CH:6]=1>C1COCC1>[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:13][C@@H:12]2[C:14](=[O:15])[CH3:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 86696501HCID 86696501, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 1490683HCID 1490683, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (0.717 mL, 3M in ether, 2.150 mmol) was added dropwise to a 0° C. solution of (1S,2S)-2-(4-fluorophenyl)-N-methoxy-N-methyl cyclopropanecarboxamide (400 mg, 1.792 mmol) in THF (15 mL). After 2 h, an additional equivalent of methylmagnesium bromide (0.717 mL, 2.150 mmol) was added. The reaction was slowly quenched with sat'd ammonium chloride (2 mL). The mixture was diluted with EtOAc, washed with H2O, washed with brine, dried over magnesium sulfate, and concentrated to give (1S,2S)-1-(2-(4-fluorophenyl)cyclopropyl)ethanone as a slightly colored oil (304 mg, 95%). 1H NMR (500 MHz, CHLOROFORM-d) δ 7.12-7.04 (m, 2H), 7.03-6.95 (m, 2H), 2.53 (ddd, J=9.1, 6.5, 4.0 Hz, 1H), 2.37-2.30 (m, 3H), 2.18 (ddd, J=8.2, 5.1, 4.0 Hz, 1H), 1.67 (ddd, J=9.2, 5.1, 4.3 Hz, 1H), 1.35 (ddd, J=8.1, 6.6, 4.3 Hz, 1H).

Workup

  1. customThe reaction was slowly quenched with sat'd ammonium chloride (2 mL)
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with H2O
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-79889b4ca77e4cfeb573ac28625d2fff
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

Loading…