Sodium Hydroxide → (3R,4S)-3,4-dimethyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid

HRID 1748262Notes

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+]>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: 70 °C

Procedure

To a solution of ethyl (3R,4S)-3,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate (851 mg, 3.0 mmol) in ethanol (20 mL) is added 1M NaOH solution (7.0 mL, 7.0 mmol). The reaction mixture is heated at 70° C. for 2 h. The solvent is removed and the residue is acidified using 1M HCl solution until the pH is 5. The resulting white solid is filtered and dried to afford the title compound (697 mg, 91%).

Workup

customThe solvent is removed
filtrationThe resulting white solid is filtered
customdried

Sources & evidence

ORD record: ord-a63d13c825904c97918a1c7af909cfbf
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150577B2

Reaction notes

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