Hydrochloric Acid → (3S,4R)-3,4-Dimethyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid

HRID 1748259Notes

Reaction equation

[CH3:1][C@H:2]1[C@@H:19]([CH3:20])[N:6]2[C:7]3[CH:8]=[C:9]([C:14]([O:16]CC)=[O:15])[CH:10]=[CH:11][C:12]=3[CH:13]=[C:5]2[C:4](=[O:21])[NH:3]1.[OH-].[Na+].Cl>C(O)C>[CH3:1][C@H:2]1[C@@H:19]([CH3:20])[N:6]2[C:7]3[CH:8]=[C:9]([C:14]([OH:16])=[O:15])[CH:10]=[CH:11][C:12]=3[CH:13]=[C:5]2[C:4](=[O:21])[NH:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of ethyl cis-3,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-α]indole-7-carboxylate (2.1 g, 7.3 mmol) in ethanol (60 mL) is added 1M NaOH solution (20 mL, 20 mmol). The reaction mixture is heated at 80° C. for 1 h and then cooled to room temperature. The reaction mixture is acidified using concentrated HCl and ethanol is removed under vacuum. The resulting solid is filtered, rinsed with water and dried to afford the title compound (1.8 g, 96%).

Workup

temperaturecooled to room temperature
customis removed under vacuum
filtrationThe resulting solid is filtered
washrinsed with water
customdried

Sources & evidence

ORD record: ord-dc6a9fe05e7c449d962bb8b46597a471
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150577B2

Reaction notes

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