Ethyl Acetate → HCID 19606342, compound

HRID 1603916Notes

Reaction equation

HRID 1603916 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:18]=3)[C:13]([CH:24]=O)=[CH:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].C(OCC)(=O)C>ClCCl.[I-].[Zn+2].[I-]>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:18]=3)[C:13]([CH3:24])=[CH:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 5003444Sodium cyanoborohydrideHCID 19606368HCID 19606368, compound

Product 1

HCID 19606342HCID 19606342, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of methyl 1-(4-phenylbutyl)-3-formylindole-5-carboxylate (600 mg, 1.79 mmol) in dry dichloromethane (15 ml) was added successively zinc iodide (857 mg, 2.69 mmol) and sodium cyanoborohydride (843 mg, 13.41 mmol). The resulting mixture was left under stirring at 85° C. for 1.5 h. After that the mixture was filtered through celite, washing the solid with dichloromethane (200 ml). The solvent was evaporated off under reduced pressure and the resulting crude was purified by chromatography through a silica gel column, eluting with n-hexane:ethyl acetate, 98:2, thereby recovering 459 mg of the title compound (80% yield).

Workup

  1. waitThe resulting mixture was left
  2. filtrationAfter that the mixture was filtered through celite
  3. washwashing the solid with dichloromethane (200 ml)
  4. customThe solvent was evaporated off under reduced pressure
  5. customthe resulting crude was purified by chromatography through a silica gel column
  6. washeluting with n-hexane

Sources & evidence

ORD record
ord-848378ced1f44b2e9186fff2643f418c
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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