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

HRID 1748262
Notes
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Reaction equation

HRID 1748262 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67234919ethyl (3R,4S)-3,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate

Product 1

HCID 67234924(3R,4S)-3,4-dimethyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. customThe solvent is removed
  2. filtrationThe resulting white solid is filtered
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes