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

HRID 1748259
Notes
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Reaction equation

HRID 1748259 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67235475Ethyl cis-3,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate

Product 1

HCID 67234926(3S,4R)-3,4-Dimethyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent
2×

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

  1. temperaturecooled to room temperature
  2. customis removed under vacuum
  3. filtrationThe resulting solid is filtered
  4. washrinsed with water
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes