Chloride → HCID 10890919, compound

HRID 1419511Notes

Reaction equation

HRID 1419511 reaction equation
[C:1]([NH:5][C:6]([C:8]1[N:9]([C:17](=[O:19])[CH3:18])[CH2:10][CH2:11][N:12]([C:14](=[O:16])[CH3:15])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].O=O>>[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][N:12]([C:14](=[O:16])[CH3:15])[CH2:11][CH2:10][N:9]1[C:17](=[O:19])[CH3:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 312ChlorideHCID 977OxygenHCID 11021867HCID 11021867, compound

Product 1

HCID 10890919HCID 10890919, compoundYield 105.4%

Procedure

10 g (37 mmol) of 1,4-diacetyl-1,4,5,6-tetrahydropyrazine-2-carboxylic acid tert-butylamide, 20.3 mg (37 μmol) of 1-[1(R)-(di-tert-butylphosphino)ethyl]-2(S)-(diphenylphosphino)ferrocene and 9.2 mg (20 μmol) of bicyclo[2.2.1]hepta-2,5-dienerhodium(I) chloride dimer were placed in an autoclave, oxygen being excluded. After flushing with argon, 80 ml of oxygen-free methanol was added. Hydrogenation was carried out at an initial pressure of 50 bar and a temperature of 110° C. for 20 hours. The autoclave was depressurized and flushed with nitrogen. The solvent of the reaction mixture was completely distilled off to give 10.50 g (95%) of the title product. GC analysis showed a conversion of 85 percent. After cleavage of the protecting groups with hydrochloric acid, the enantioselectivity of the hydrogenation was determined by GC analysis, giving an ee of 90.5 percent.

Workup

  1. customAfter flushing with argon, 80 ml of oxygen-free methanol
  2. additionwas added
  3. customflushed with nitrogen
  4. distillationThe solvent of the reaction mixture was completely distilled off

Sources & evidence

ORD record
ord-88bb76fd075249a89a63188a231c907a
Source dataset
uspto-grants-1999_03
Patent number
US05886181

Reaction notes

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