Hydrochloric Acid → (R)-2-Methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acid methyl ester

HRID 447083Notes

Reaction equation

HRID 447083 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C@H:12]2[CH3:24])=[N:9][CH:10]=1)=[O:4].Cl>CO>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]2[CH3:24])=[N:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67179448HCID 67179448, compound

Product 1

HCID 67179051(R)-2-Methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acid methyl esterYield 85.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (R)-2-methyl-4-boc-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-carboxylic acid methyl ester (2 g, 5.94 mmol) in MeOH (17 mL) is added HCl (4M in dioxane, 4.5 mL, 18 mmol). The reaction mixture is stirred at 70° C. for 1 h. The reaction solution is concentrated, dissolved in DCM and organic layer is washed with Na2CO3 to adjust the pH value to 8.0. The solvents are removed under reduced pressure to afford a brown oil (1.2 g, 77%).

Workup

  1. concentrationThe reaction solution is concentrated
  2. dissolutiondissolved in DCM
  3. washorganic layer is washed with Na2CO3
  4. customThe solvents are removed under reduced pressure

Sources & evidence

ORD record
ord-0f8303dcfcd24dfd9e03792ce27b4021
Source dataset
uspto-grants-2013_07
Patent number
US08481542B2

Reaction notes

Loading…