Ethyl Acetate → HCID 67363091, compound

HRID 1916599Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=O)[CH:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])=[N:12][CH:13]=1.CCOC(C)=O.[OH-].[Na+]>C1COCC1.O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][CH2:15][CH:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])=[N:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere 6.00 mL (6.00 mmol) 1 M lithium aluminium hydride solution in THF are added to a solution, cooled to 0° C., of 1.8 g (6.04 mmol) N-(5-bromo-pyridin-2-yl)-2-pyrrolidin-1-yl-propionamide in 30 mL THF, in such a way that the internal temperature does not exceed 4° C. The reaction solution is stirred for a further 20 min at 0° C. EtOAc is carefully added, the aluminium complex is decomposed with 0.2 mL water, then with 0.2 mL 15% sodium hydroxide solution solution and finally with 0.6 mL water. The precipitate formed is suction filtered and the filtrate is diluted with 50 mL EtOAc. The organic phase is washed with 30 mL saturated NaHCO3 solution and dried over MgSO4. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (EtOAc/MeOH/NH3 9:1:0.1).

Workup

customdoes not exceed 4° C
customThe precipitate formed
filtrationfiltered
additionthe filtrate is diluted with 50 mL EtOAc
washThe organic phase is washed with 30 mL saturated NaHCO3 solution
dry with materialdried over MgSO4
customand further purification

Sources & evidence

ORD record: ord-8109cac9fdee4a33aa13939a4f42127a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Reaction notes

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