4-Chloropyridine → tert-Butyl 8-(pyridin-4-yl)-2,8-diazaspiro[4,5]decane-2-carboxylate

HRID 2387935Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.Cl[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1.C(=O)([O-])O.[Na+]>CC(O)C>[N:31]1[CH:32]=[CH:33][C:28]([N:15]2[CH2:16][CH2:17][C:10]3([CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:12][CH2:11]3)[CH2:13][CH2:14]2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 90 °C

Procedure

tert-Butyl-2,8-diazaspiro[4.5]decane-2-carboxylate (10.403 mmol, 1 equiv.) and N-ethyl-diisopropylamine (41.608 mmol, 4 equiv.) were placed in 2-propanol (20 ml). 4-Chloropyridine (31.206 mmol, 3 equiv.) was added, and the mixture was heated for 16 hours at 90° C. Saturated sodium hydrogen carbonate solution (50 ml) was then added, and the phases were separated. The aqueous phase was extracted with ethyl acetate (4×50 ml), and the combined organic phases were washed with saturated NaCl solution (50 ml) and dried over magnesium sulfate. After purification by column chromatography (ethyl acetate/DCM/methanol/ammonia (25% aq), 100:100:25:1), the desired product was obtained in the form of a yellow oil. Yield: 1.8 g (55%)

Workup

customthe phases were separated
extractionThe aqueous phase was extracted with ethyl acetate (4×50 ml)
washthe combined organic phases were washed with saturated NaCl solution (50 ml)
dry with materialdried over magnesium sulfate
customAfter purification by column chromatography (ethyl acetate/DCM/methanol/ammonia (25% aq), 100:100:25:1)

Sources & evidence

ORD record: ord-cb0299c74d314b17bbd1cdaf78dfb7bc
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269000B2

Reaction notes

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