Sodium hydride → 3-Bromo-1-t-butoxycarbonylmethyl-7-phenylperhydroazepin-2-one

HRID 845334Notes

Reaction equation

HRID 845334 reaction equation
[Br:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:4][C:3]1=[O:15].I[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[H-].[Na+]>O1CCCC1>[Br:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:3]1=[O:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11021060Tert-butyl 2-iodoacetateHCID 140034323-Bromo-7-phenyl-hexahydroazepin-2-one

Product 1

HCID 190376153-Bromo-1-t-butoxycarbonylmethyl-7-phenylperhydroazepin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 15.5 g of the lactam from Step A and 14.7 t-butyl iodoacetate in 150 ml tetrahydrofuran was added dropwise to a slurry of 1.45 g sodium hydride in 20 ml tetrahydrofuran. After 3 hr at room temperature the reaction was quenched by the addition of 15 ml sat. NH4Cl solution. The mixture was filtered and concentrated and the residue partitioned between CHCl3 and H2O. The crude product was obtained after drying and concentrating the CHCl3 solution. Chromatography over silica gel with hexane: ethyl acetate (4:1) afforded two isomers of 3-bromo-1-t-butoxycarbonylmethyl-7-phenylperhydroazepin-2-one: isomer A (minor, elutes first), and isomer B (major, elutes second).

Workup

  1. customAfter 3 hr at room temperature the reaction was quenched by the addition of 15 ml sat. NH4Cl solution
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customthe residue partitioned between CHCl3 and H2O
  5. customThe crude product was obtained
  6. customafter drying
  7. concentrationconcentrating the CHCl3 solution

Sources & evidence

ORD record
ord-26c9f60479d64fa884643024589ee824
Source dataset
uspto-grants-1988_07
Patent number
US04757068

Reaction notes

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