Ethyl Acetate → HCID 86674686, compound

HRID 571826Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1Br.[C:22]([Cu])#[N:23].CCOC(C)=O>CN1C(=O)CCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1[C:22]#[N:23]

Participants

Conditions

Temperature: 160 °C

Procedure

To a stirred solution of tert-butyl (RS)-2-(4-amino-3-bromophenyl)morpholine-4-carboxylate (3.76 g) in NMP (30 ml) was added CuCN (1.77 g) and the reaction mixture was then stirred at 160° C. for 5 h. The mixture was then cooled to room temperature and poured into EtOAc. The resulting suspension was filtered through sintered glass and the filtrate was extracted sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 60% EtOAc in heptane) to afford tert-butyl (RS)-2-(4-amino-3-cyanophenyl)morpholine-4-carboxylate (659 mg, 21%) as a yellow solid. MS (ISP): 321.2 ([M+NH4]+), 304.2 ([M+H]+).

Workup

temperatureThe mixture was then cooled to room temperature
filtrationThe resulting suspension was filtered through sintered glass
extractionthe filtrate was extracted sequentially with water and with saturated brine
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography (silica gel; gradient: 0% to 60% EtOAc in heptane)

Sources & evidence

ORD record: ord-a41539506d724a53a24a7d5d7d2bdde8
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029370B2

Reaction notes

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