Triethylamine → Tert-butyl 9-[5-(methoxycarbonyl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane-3-carboxylate

HRID 1984789

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.CCN(CC)CC.[CH2:19]1[C:24]2([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][CH2:22][N:21]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:20]1.CCOC(C)=O>CS(C)=O>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([N:27]2[CH2:28][CH2:29][C:24]3([CH2:23][CH2:22][N:21]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH2:20][CH2:19]3)[CH2:25][CH2:26]2)=[N:3][CH:4]=1)=[O:7]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 6-chloronicotinate (800 mg, 3.15 mmol), NEt3 (1.00 mL, 7.19 mmol) and tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate (1.00 g, 3.94 mmol) in 5 mL of DMSO was heated to 100° C. for 1 h with microwave irradiation. The reaction mixture was poured into EtOAc and washed with 2 N NaOH, 2 H HCl, brine and dried (Na2SO4), filtered and concentrated giving tert-butyl 9-[5-(methoxycarbonyl)pyridin-2-yl]-3,9-diazaspiro[5.5]undecane-3-carboxylate.

Workup

washwashed with 2 N NaOH, 2 H HCl, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-e1315ea851c3454496227741dd07c4fa
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544695B2

Linked notes

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