Oxygen → HCID 54564975, compound

HRID 1419513Notes

Reaction equation

HRID 1419513 reaction equation
[C:1]([NH:5][C:6]([C:8]1[N:9]([C:16](=[O:19])[CH2:17][CH3:18])[CH2:10][CH2:11][N:12]([CH:14]=[O:15])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O=O>>[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][N:12]([CH:14]=[O:15])[CH2:11][CH2:10][N:9]1[C:16](=[O:19])[CH2:17][CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 977OxygenHCID 53652740HCID 53652740, compound

Product 1

HCID 54564975HCID 54564975, compoundYield 104.8%

Procedure

16.1 g (60.2 mmol) of 4-formyl-1-propionyl-1,4,5,6-tetrahydropyrazine-2-carboxylic acid tert-butylamide, 19.5 mg (35.9 μmol) of 1-[1(R)-(di-tert-butylphosphino)-ethyl]-2(S)-(diphenylphosphino)ferrocene and 11.1 mg (29.6 μmol) of bis(bicyclo[2.2.1]hepta-2,5-diene)rhodium(I) tetrafluoroborate 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 12 bar and a temperature of 90° C. for 8 hours. The autoclave was depressurized and flushed with nitrogen. The solvent of the reaction mixture was completely distilled off to give 17.00 g (94%) of the title product. GC analysis showed a conversion of 99 percent. After cleavage of the protecting groups with hydrochloric acid, the enantioselectivity of the hydrogenation was determined by GC analysis, giving an ee of 96.5 percent. The melting point of the title compound was: 132.1° to 134.3° C. Other data concerning the title compound was:

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-a132475b455a48288b5ca0054325c8c8
Source dataset
uspto-grants-1999_03
Patent number
US05886181

Reaction notes

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