Hydrochloric Acid → 7,7-dimethyl-1-oxo-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizine-9-carboxylic acid

HRID 520309Notes

Reaction equation

[CH3:1][C:2]1([CH3:19])[CH2:9][C:8]2[N:4]([C:5]3[CH2:17][CH2:16][NH:15][C:14](=[O:18])[C:6]=3[C:7]=2[C:10]([O:12]C)=[O:11])[CH2:3]1.[Li+].[OH-].Cl>C1COCC1.O>[CH3:1][C:2]1([CH3:19])[CH2:9][C:8]2[N:4]([C:5]3[CH2:17][CH2:16][NH:15][C:14](=[O:18])[C:6]=3[C:7]=2[C:10]([OH:12])=[O:11])[CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 137l (crude, 35.4 mmol) in THF/H2O (100 mL/100 mL) was added LiOH (4.26 g, 177 mmol). See FIG. 2. The mixture was stirred at 50° C. for 1 h. Upon reaction completion, the mixture was acidified with HCl (1N) until pH<6 and concentrated to remove THF. The resulting white solid was collected by filtration and washed with cold water to give 7,7-dimethyl-1-oxo-2,3,4,6,7,8-hexahydro-1H-pyrido[3,4-b]pyrrolizine-9-carboxylic acid 137m (8 g, 91%).

Workup

customUpon reaction completion
concentrationconcentrated
customto remove THF
filtrationThe resulting white solid was collected by filtration
washwashed with cold water

Sources & evidence

ORD record: ord-f46af9ee2601478cb24b9231d5dfd6c4
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326985B2

Reaction notes

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