Potassium Cyanide → HCID 15391053, compound

HRID 849668Notes

Reaction equation

HRID 849668 reaction equation
[CH:1]([C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)=O.[C:11]1([C@@H:17]([NH2:19])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C-:20]#[N:21].[K+].S([O-])(O)=O.[Na+]>C(O)C.O>[C:20]([CH:1]([NH:19][C@H:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:18])[C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)#[N:21]

Participants

7

Reactant 4

HCID 9032Potassium CyanideHCID 758181-Phenethylamine, (-)-HCID 9964122Ethyl 1-formylcyclopropanecarboxylateHCID 23665763Sodium Bisulfite

Product 1

HCID 15391053HCID 15391053, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

An eggplant type flask was charged with 10 g of ethyl 1-formylcyclopropane-1-carboxylate to which were further added 12.8 g of (S)-1-phenylethylamine dissolved in 100 ml of ethanol, 6.9 g of potassium cyanide dissolved in 40 ml of water and 22 g of sodium hydrogen sulfite in that order at 0° C. The reaction system was stirred for 2 hours at 50° C. After confirming completion of the reaction, the reaction solution was mixed with ice water and extracted with ethyl acetate. Next, the resulting organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate and, after removing insoluble matter by filtration, the solvent was evaporated under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography (hexane:ethyl acetate=8:1) to obtain 15.7 g (82%) of a diastereomer mixture in the form of colorless oil. Formation ratio of the two diastereomers was calculated under the following analytical conditions. Further, these diastereomers were able to be separated by a thin layer chromatography (hexane:ethyl acetate=4:1).

Workup

  1. customat 0° C
  2. customcompletion of the reaction
  3. extractionextracted with ethyl acetate
  4. washNext, the resulting organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter removing insoluble matter
  7. filtrationby filtration
  8. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-ccf45146d21641b7a6e5876b51e85d4c
Source dataset
uspto-grants-2000_01
Patent number
US06013806

Reaction notes

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