Sodium hydride → methyl 2-oxo-1-(trimethylsilanylethoxymethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-9-carboxylate

HRID 1176597Notes

Reaction equation

[O:1]=[C:2]1[NH:8][C:7]2[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][CH2:4][CH2:3]1.[H-].[Na+].[CH3:19][Si:20]([CH3:27])([CH3:26])[CH2:21][CH2:22][O:23][CH2:24]Cl.C(=O)([O-])O.[Na+]>CN(C)C=O>[O:1]=[C:2]1[N:8]([CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH3:27])([CH3:26])[CH3:19])[C:7]2[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

2.500 g of methyl 2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-9-carboxylate are dissolved under argon in 30 ml of N,N-dimethylformamide and the solution is cooled to 0° C. in an ice bath. 0.600 g of sodium hydride dispersion (60%) is added in portions and the reaction mixture is subsequently stirred at 0° C. over a further 1 hour. 0.502 ml of 2-(trimethylsilyl)ethoxymethyl chloride is added and the reaction mixture is subsequently stirred at room temperature over 11 hours. The reaction mixture is poured onto 150 ml of saturated aqueous sodium hydrogencarbonate solution and extracted with 2×150 ml of tert-butyl methyl ether. The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a reddish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.35 (1:1 EtOAc-heptane); Rt=5.02.

Workup

stirringthe reaction mixture is subsequently stirred at room temperature over 11 hours
extractionextracted with 2×150 ml of tert-butyl methyl ether
dry with materialThe combined organic phases are dried over sodium sulphate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-e92c9576896a4d9a86eda5158434931e
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842688B2

Reaction notes

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