Water → 7-(3-Benzyloxy-4-nitrobenzyl)-azepan-2-one

HRID 660551Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[N:19]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[OH2:33]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[CH2:12][CH:13]1[NH:19][C:14](=[O:33])[CH2:15][CH2:16][CH2:17][CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -50 °C

Procedure

To a solution of 2-(3-benzyloxy-4-nitrobenzyl)-cyclohexanone oxime (250 mg, 0.706 mmol) in chloroform (5 mL) at −50° C. is added PCl5 (148 mg, 0.71 mmol). The mixture is stirred at −50° C. for 2 h then water is added. The mixture is extracted with methylene chloride and the organic phase is washed sequentially with 5% NaOH, water and brine. The organic solution is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by flash chromatography using a gradient of 50-100% EtOAc/hexanes to afford the title compound: (M+1)+=355.

Workup

extractionThe mixture is extracted with methylene chloride
washthe organic phase is washed sequentially with 5% NaOH, water and brine
dry with materialThe organic solution is dried over sodium sulfate
customthe solvent is removed under reduced pressure
customThe residue is purified by flash chromatography

Sources & evidence

ORD record: ord-237bca27c3f84349af0fe380ed8eab1b
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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