Oxygen → HCID 10890919, compound

HRID 1419512Notes

Reaction equation

HRID 1419512 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].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

3

Reactant 2

HCID 977OxygenHCID 11021867HCID 11021867, compound

Product 1

HCID 10890919HCID 10890919, compoundYield 130.4%

Procedure

8.00 g (29.9 mmol) of 1,4-diacetyl-1,4,5,6-tetrahydropyrazine-2-carboxylic acid tert-butylamide, 10.0 mg (18 μmol) of 1-[1(R)-(di-tert-butylphosphino)-ethyl]-2(S)-(diphenylphosphino)ferrocene and 6.0 mg (16 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 50 bar and a temperature of 110° C. for 20 hours. Working-up of the reaction mixture analogously to Example 19 gave 10.50 g (75%) of the title product. GC analysis showed a conversion of 97 percent. After cleavage of the protecting groups with hydrochloric acid, the enantioselectivity of the hydrogenation was determined by GC analysis, giving an ee of 90.7 percent. The melting point of the title compound was: 139.9° to 150.6° C. Other data concerning the title compound was:

Workup

  1. customAfter flushing with argon, 80 ml of oxygen-free methanol
  2. additionwas added

Sources & evidence

ORD record
ord-8d3babfce75143c69b584523cd069c2b
Source dataset
uspto-grants-1999_03
Patent number
US05886181

Reaction notes

Loading…