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

HRID 1643447Notes

Reaction equation

[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].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:8]2[CH2:7][CH2:6][C:5]3([CH2:1][N:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:4]3)[CH2:10][CH2:9]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 eq) and N-ethyl-diisopropylamine (41.608 mmol, 4 eq) were dissolved in 2-propanol (20 ml). 4-Chloropyridine (31.206 mmol, 3 eq) was added and the mixture was heated at 90° C. for 16 h. Saturated sodium bicarbonate solution (50 ml) was added and the phases were separated. The aqueous phase was extracted with ethyl acetate (4×50 ml) and the combined org. phases were washed with saturated sodium chloride solution (50 ml), dried over magnesium sulfate and concentrated. After purification by column chromatography (silica gel, ethyl acetate/methylene chloride/methanol/ammonia (25% aq) (100:100:25:1), the desired product was obtained as a yellow oil. Yield: 1.8 g (55%)

Workup

customthe phases were separated
extractionThe aqueous phase was extracted with ethyl acetate (4×50 ml)
washphases were washed with saturated sodium chloride solution (50 ml)
dry with materialdried over magnesium sulfate
concentrationconcentrated
customAfter purification by column chromatography (silica gel, ethyl acetate/methylene chloride/methanol/ammonia (25% aq) (100:100:25:1)

Sources & evidence

ORD record: ord-5251c56164b54f748c252f812606ee21
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119805B2

Reaction notes

Loading…