HCID 15123261, compound → HCID 131717375, compound

HRID 1196526Notes

Reaction equation

HRID 1196526 reaction equation
[N:1]1([CH2:6][C:7]2[N:12]=[CH:11][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C(O)(=O)C.O=[Pt]=O>[N:1]1([CH2:6][C@H:7]2[NH:12][CH2:11][C@@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 15123261HCID 15123261, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131717375HCID 131717375, compoundYield 118.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of the product of stage (i) (4.1 g) in glacial acetic acid (80 ml) was hydrogenated at 22° and atmospheric pressure over Adams' catalyst (3 g). After 3 h the uptake of hydrogen was complete and the mixture was filtered. The filtrate was evaporated to leave an oil which was partitioned between 2N sodium carbonate solution (100 ml) and dichloromethane (100 ml). The aqueous phase was further extracted with dichloromethane (100 ml). The combined organic extracts were washed with saturated brine, dried and evaporated to leave an oil (5.0 g). The oil was purified by flash chromatography eluting with a mixture of dichloromethane, ethanol and ammonia (200:8:1) to give the title compound as an oil (2.6 g). N.m.r.-indicates mixture of cis:trans (3:1). T.l.c. Silica (Dichloromethane:ethanol: 0.88 ammonia 100:8:1) Rf 0.4.

Workup

  1. customwas hydrogenated at 22°
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated
  4. customto leave an oil which
  5. customwas partitioned between 2N sodium carbonate solution (100 ml) and dichloromethane (100 ml)
  6. extractionThe aqueous phase was further extracted with dichloromethane (100 ml)
  7. washThe combined organic extracts were washed with saturated brine
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-e3c48ba88e0e4b8ebab2a8d45e446846
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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