Ethyl Acetate → 2-{6-[3-(2-Methylpyrrolidin-1-yl)propoxy]pyridin-3-yl}-3-oxa-1-azaspiro[4.5]dec-1-ene

HRID 251450Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:12][CH2:11][C:10]3([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[N:9]=2)=[CH:4][CH:3]=1.C([O-])(C)(C)C.[K+].[CH3:24][CH:25]1[CH2:29][CH2:28][CH2:27][N:26]1[CH2:30][CH2:31][CH2:32][OH:33].C(OCC)(=O)C>O1CCCC1>[CH3:24][CH:25]1[CH2:29][CH2:28][CH2:27][N:26]1[CH2:30][CH2:31][CH2:32][O:33][C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:12][CH2:11][C:10]3([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-(6-chloropyridin-3-yl)-3-oxa-1-azaspiro[4.5]dec-1-ene ax49 (0.109 g, 0.76 mmol, 1 eq) and potassium tert-butanolate (0.102 g, 0.91 mmol, 1.2 eq) are added to a cold (0° C.) solution of 3-(2-methylpyrrolidin-1-yl)propan-1-ol (0.2 g, 0.8 mmol, 1.05 eq) in tetrahydrofuran (4 ml). The mixture is stirred under microwave irradiation (150 W) at 60° C. for 21 min. Ethyl acetate is then added. The organic layer is washed with a saturated solution of sodium hydrogenocarbonate, dried over magnesium sulfate and the solvent is removed under vacuum to give 0.227 g of yellow oil. The oil is purified over silica (eluent: dichloromethane/methanol/ammonia 97:2.7:0.3) to give 0.149 g of 2-{6-[3-(2-methylpyrrolidin-1-yl)propoxy]pyridin-3-yl}-3-oxa-1-azaspiro[4.5]dec-1-ene 16 as a yellow oil.

Workup

washThe organic layer is washed with a saturated solution of sodium hydrogenocarbonate
dry with materialdried over magnesium sulfate
customthe solvent is removed under vacuum

Sources & evidence

ORD record: ord-54a2f902b06f4423b14235525744d808
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863450B2

Reaction notes

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