Potassium Cyanide → HCID 86590956, compound

HRID 1791984Notes

Reaction equation

HRID 1791984 reaction equation
[OH:1][CH2:2][C:3]1([CH:6]=O)[CH2:5][CH2:4]1.[C:8]1([C@@H:14]([NH2:16])[CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C-:17]#[N:18].[K+].S(=O)(O)[O-].[Na+].C(=O)(O)[O-].[Na+]>O.C(O)C>[OH:1][CH2:2][C:3]1([CH:6]([NH:16][C@H:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:15])[C:17]#[N:18])[CH2:5][CH2:4]1

Participants

8

Reactant 5

HCID 9032Potassium CyanideHCID 758181-Phenethylamine, (-)-HCID 516892Sodium BicarbonateHCID 23539487HCID 23539487, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 86590956HCID 86590956, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To an ethanol (4.9 mL) solution of 1-(hydroxymethyl)cyclopropane carboaldehyde (683 mg, 6.82 mmol) were added water (2.1 mL), (S)-(−)-1-phenylethylamine (0.94 mL, 7.50 mmol), potassium cyanide (489 mg, 7.50 mmol) and sodium bisulfite (1.45 g, 13.6 mmol). The mixture was stirred at 50° C. for 30 minutes. After cooling to 0° C., a saturated aqueous solution of sodium bicarbonate was added to terminate the reaction, followed by extraction with ethyl acetate. The organic layer was washed with water and then dried over magnesium sulfate. The solvent was and evaporated under reduced pressure, whereby the title compound was obtained as a pale yellow oil (1.55 g, crude product).

Workup

  1. temperatureAfter cooling to 0° C.
  2. customto terminate
  3. customthe reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure, whereby the title compound
  8. customwas obtained as a pale yellow oil (1.55 g, crude product)

Sources & evidence

ORD record
ord-8fc002d690874d13a0c63471e87da354
Source dataset
uspto-grants-2006_07
Patent number
US07074837B2

Reaction notes

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