Diethyl Ether → 1,1-Dimethylethyl 3-(3,5-difluorobenzoyl)-1-azetidinecarboxylate

HRID 602664Notes

Reaction equation

HRID 602664 reaction equation
CON(C)[C:4]([CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5].[F:18][C:19]1[CH:20]=[C:21]([Mg]Br)[CH:22]=[C:23]([F:25])[CH:24]=1.CCOCC>C1COCC1>[F:18][C:19]1[CH:20]=[C:21]([CH:22]=[C:23]([F:25])[CH:24]=1)[C:4]([CH:6]1[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:9]1)=[O:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21306970tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylateHCID 178505930HCID 178505930, compound

Product 1

HCID 670659051,1-Dimethylethyl 3-(3,5-difluorobenzoyl)-1-azetidinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.19 g (4.87 mmol) of tert-butyl 3-{[methoxy(methyl)amino]carbonyl}azetidine-1-carboxylate in 15 mL of THF was added to a solution of 14.6 mL (7.31 mmol) of 3,5-difluorophenylmagnesium bromide (0.5M in THF). The reaction mixture was stirred for 2 h at 0° C., then poured into 100 mL of ether and washed with 10 mL of water. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography with hexanes/ethyl acetate to afford the title compound. 1NMR (CDCl3) δ 1.48 (s, 9H), 4.08 (m, 1H), 4.24 (m, 4H), 7.36 (m, 1H), 7.38 (m, 2H).

Workup

  1. washwashed with 10 mL of water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-5c619e18c5b24dacb9521b8258c92655
Source dataset
uspto-grants-2011_03
Patent number
US07906503B2

Reaction notes

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