Water → HCID 22004845, compound

HRID 1636604Notes

Reaction equation

HRID 1636604 reaction equation
[CH2:1]([C:4]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])=[CH:7][NH:8]2)[CH:2]=[CH2:3].C([BH3-])#N.[Na+].O>C(O)(=O)C>[CH2:1]([C:4]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]([CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH2:7][NH:8]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 22004814HCID 22004814, compound

Product 1

HCID 22004845HCID 22004845, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of N-[2-(4-allyl-5-hydroxyindol-3-yl)ethyl]propionamide (3.73 g, 14.3 mmol) in acetic acid (20 mL) was added sodium cyanoborohydride (2.7 g, 43.0 mmol) portionwise maintaining the reaction temperature around 15° C. The mixture was stirred for 1 hour maintaining the temperature 15 to 20° C. and then poured into water. The product was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, brine and water, dried over anhydrous magnesium sulfate and evaporated to afford the title compound. This compound was used for the subsequent reaction without further purification.

Workup

  1. temperaturemaintaining the temperature 15 to 20° C.
  2. extractionThe product was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, brine and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ec92d98aefce4fda844315aae0f1324f
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

Loading…