Trifluoroacetic acid → 9-Benzyl-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 1106918Notes

Reaction equation

HRID 1106918 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH2:17][CH2:18][N:19](C(OC(C)(C)C)=O)[CH2:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH2:17][CH2:18][NH:19][CH2:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 183772769-benzyl-2-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

Product 1

HCID 5986499-Benzyl-2,3,4,9-tetrahydro-1H-beta-carboline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 9-benzyl-2-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]-indole (3.66 g, 10.1 mmol) in chloroform (50 ml) was stirred with trifluoroacetic acid (20 ml) at room temperature for 2 hours. The mixture was evaporated to dryness and the residue partitioned between chloroform and saturated potassium carbonate solution (150 ml/1:2). The organic layer was separated and dried (MgSO4). Filtration and evaporation of the solvent gave the product. (2.66 g, 100%).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue partitioned between chloroform and saturated potassium carbonate solution (150 ml/1:2)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and evaporation of the solvent
  6. customgave the product

Sources & evidence

ORD record
ord-7c4e0589adce453093174e580badcbc9
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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