Benzyl chloroformate → Benzyl 1-(4-fluorophenyl)-2-oxoazepane-3-carboxylate

HRID 2241378Notes

Reaction equation

HRID 2241378 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:15])=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[C:9]2=[O:15])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 2724682Lithium diisopropylamideHCID 675158001-(4-Fluorophenyl)azepan-2-one

Product 1

HCID 68517020Benzyl 1-(4-fluorophenyl)-2-oxoazepane-3-carboxylateYield 55.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4-fluorophenyl)azepan-2-one (1.1 g, 5.3 mmol) was dissolved in THF (5 mL) and was added into LDA (11 mmol) at −78° C. and stirred for 5 minutes. Benzyl chloroformate (1.6 ml, 11 mmol) was added at −78° C. and the reaction warmed to ambient temperature. The solution was poured into ice and diluted with EtOAc (100 mL). The organic layer washed with brine, dried with Na2SO4, filtered and concentrated. The residue was purified by column chromatography (50% EtOAc in hexane) to afford the product (1 g, 55% yield) as brown oil.

Workup

  1. additionThe solution was poured into ice
  2. washThe organic layer washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-2f7e45f320bc45df8583e7697861fcb5
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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