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

HRID 1748263Notes

Reaction equation

HRID 1748263 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

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 98.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

Ethyl (3S,4R)-3,4-dimethyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate (870 mg, 3.0 mmol) is suspended in ethanol (25 mL) and 1M NaOH solution (7.6 mL, 7.6 mmol) is added. The reaction mixture is heated at 80° C. for 1 h and then cooled to room temperature. The mixture is acidified with 1M HCl solution and ethanol is removed. The resulting solid is filtered, rinsed with water and dried to afford the title compound (760 mg, 97%).

Workup

  1. temperaturecooled to room temperature
  2. customis removed
  3. filtrationThe resulting solid is filtered
  4. washrinsed with water
  5. customdried

Sources & evidence

ORD record
ord-04ddfd92feb54c63809c44560ff6eb74
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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