Acetic Acid → HCID 66993348, compound

HRID 1953533Notes

Reaction equation

HRID 1953533 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:35])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][C:29]([CH:32]=[N:33][CH3:34])=[CH:28][CH:27]=3)=[CH:4][C:3]=2[O:2]1.[BH3-]C#N.[Na+].C(O)(=O)C>CO>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:35])/[CH:24]=[CH:25]/[C:26]3[CH:27]=[CH:28][C:29]([CH2:32][NH:33][CH3:34])=[CH:30][CH:31]=3)=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 70109926HCID 70109926, compound

Product 1

HCID 66993348HCID 66993348, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-1-[1-(3,4-methylenedioxyphenyl)-1,3,4,9-tetrahydro-β-carbolin-2-yl]-3-(4-methyliminomethylphenyl)propene-1-one (0.46 g, 1.1 mmol), NaBH3CN (0.14 g, 2.3 mmol) and acetic acid (0.11 mL) in 20 mL of MeOH was stirred at rt for one hour. The reaction mixture was quenched with 50 mL of an aqueous saturated solution of NaHCO3. Extraction with 2×30 mL of DCM, washing with brine, drying over Na2SO4 and concentration in vacuo gave a residue that was purified via flash chromatography of silica gel using DCM:MeOH (97.3) as eluting solvent. Recrystallization from DCM:cyclohexane gave the title compound (0.05 g, 10%) as a white powder.

Workup

  1. customThe reaction mixture was quenched with 50 mL of an aqueous saturated solution of NaHCO3
  2. extractionExtraction with 2×30 mL of DCM
  3. washwashing with brine
  4. dry with materialdrying over Na2SO4 and concentration in vacuo
  5. customgave a residue that
  6. customwas purified via flash chromatography of silica gel
  7. washMeOH (97.3) as eluting solvent
  8. customRecrystallization from DCM

Sources & evidence

ORD record
ord-9fbc38e3be90417187768942fe142656
Source dataset
uspto-grants-2000_09
Patent number
US06117881

Reaction notes

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