Acetic Acid → HCID 66993348, compound

HRID 1637891Notes

Reaction equation

HRID 1637891 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 rL 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. MP: 201° C.

Workup

  1. customThe reaction mixture was quenched with 50 rL 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. washas eluting solvent
  8. customRecrystallization from DCM

Sources & evidence

ORD record
ord-4d9837bffa2342599b0db4e967bb337b
Source dataset
uspto-grants-2000_03
Patent number
US06043252

Reaction notes

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