Diethyl Ether → [4-(2-Methoxy-pyridin-3-yl)-4-oxo-butyl]-carbamic acid tert-butyl ester

HRID 352136

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(NC(C)C)(C)C.C[Li].COCN[C:22](=O)[CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].C[CH2:35][O:36]CC>O1CCCC1>[CH3:31][C:28]([O:27][C:26](=[O:32])[NH:25][CH2:24][CH2:23][CH2:22][C:35]([C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:36])([CH3:29])[CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Methoxypyridine (1.9 ml) and then diisopropylamine (0.1 ml) were added to a solution of methyl lithium (10 ml of a 1.6M solution in ether) in tetrahydrofuran (20 ml) at −78° C. and the solution was stirred at 0° C. for 18hand then re-cooled to −78° C. A solution of 1,1-dimethylethyl [3-(methoxymethylamino)-3-oxopropyl]-carbamate (1.6 g) in tetrahydrofuran (5 ml) was added slowly and the resultant solution was allowed to warm to −30° C. over 3.5 h, quenched with aqueous ammonium chloride and extracted with ether (three times). The combined organic extracts were dried (sodium sulphate), evaporated and purified by chromatography on silica eluting with petrol-ether gave the sub-title compound as a colourless oil (0.572 g).

Workup

temperaturethen re-cooled to −78° C
temperatureto warm to −30° C. over 3.5 h
customquenched with aqueous ammonium chloride
extractionextracted with ether (three times)
dry with materialThe combined organic extracts were dried (sodium sulphate)
customevaporated
custompurified by chromatography on silica eluting with petrol-ether

Sources & evidence

ORD record: ord-3e38315d28f442a38cbf626afe239183
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743939B2

Linked notes

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