Allyl bromide → 1-Allyl-3-ethyl-3-(3-benzyloxy-phenyl)-azepan-2-one

HRID 1594913Notes

Reaction equation

[CH2:1]([C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]1=[O:10])[CH3:2].[H-].[Na+].[CH2:27](Br)[CH:28]=[CH2:29]>CN(C=O)C>[CH2:29]([N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C:3]([CH2:1][CH3:2])([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=2)[C:4]1=[O:10])[CH:28]=[CH2:27]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-ethyl-3-(3-benzyloxy-phenyl)-azepan-2-one, as described above in Step A, (1.65 g, 5.1 mmol) in DMF (25 mL) at 0° C. was added NaH (0.265 g, 6.63 mmol) and the mixture was stirred for 20 min at 0° C. and 20 min at 25° C. Allyl bromide (0.66 mL, 7.65 mmol) was added. After 5 hr, additional NaH (0.13 g, 3 mmol) and allyl bromide (0.33 mL, 3.5 mmol) were added and stirring was continued for 16 hr. The reaction was quenched with H2O and the solvents removed in vacuo . The residue was partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was separated, washed with brine and dried (MgSO4). Filtration and concentration gave the title compound after chromatography on silica gel with hexane and ethyl acetate 9:1.

Workup

waitAfter 5 hr
stirringstirring
waitwas continued for 16 hr
customThe reaction was quenched with H2O
customthe solvents removed in vacuo
customThe residue was partitioned between EtOAc and saturated NaHCO3 solution
customThe organic layer was separated
washwashed with brine
dry with materialdried (MgSO4)
filtrationFiltration and concentration

Sources & evidence

ORD record: ord-f6481199bb344b32b3a90b4ad3d0ea87
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06284755B1

Reaction notes

Loading…