Caprolactam → 2H-Azepine, 3,4,5,6-tetrahydro-7-methoxy-

HRID 1619375Notes

Reaction equation

HRID 1619375 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:8].F[B-](F)(F)F.[CH3:14][O+](C)C>C(Cl)Cl>[CH3:14][O:8][C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:1]=1

Participants

4

Reactant 2

HCID 7768CaprolactamHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)

Product 1

HCID 756572H-Azepine, 3,4,5,6-tetrahydro-7-methoxy-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of azepan-2-one (5.0 g, 44 mmol) and trimethyloxonium tetrafluoroborate (7.8 g, 53 mmol) in DCM (30 mL) was stirred at room temperature for 12 h. Then the reaction mixture was quenched with saturated sodium carbonate (50 mL) and extracted with DCM (3×100 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the desired product. MS (ESI): 128 (MH+).

Workup

  1. customThen the reaction mixture was quenched with saturated sodium carbonate (50 mL)
  2. extractionextracted with DCM (3×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-155c4fc3dcf2497e9cdfd7589a5df7d6
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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