Benzyl chloroformate → 1,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

HRID 1106913Notes

Reaction equation

HRID 1106913 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH2:12]1[C:17]2[NH:18][C:19]3[C:24]([C:16]=2[CH2:15][CH2:14][NH:13]1)=[CH:23][CH:22]=[CH:21][CH:20]=3.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH2:5]([O:4][C:2]([N:13]1[CH2:14][CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH2:12]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 107838Tetrahydro-beta-carbolineHCID 516892Sodium Bicarbonate

Product 1

HCID 110667371,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Benzyl chloroformate (1.8 ml, 12.6 mmol) was added to a solution of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (1.72 g, 10.0 mmol) and sodium bicarbonate (1.85 g, 22.0 mmol) in dioxan (50 ml) at room temperature. The mixture was stirred at room temperature for 16 hours, concentrated in vacuo and the residue dissolved in water (50 ml). The aqueous mixture was extracted with chloroform (3×50 ml), and the combined extracts dried (MgSO4). Filtration and evaporation of the solvent gave the crude product which was purified by chromatography on silica gel with hexane-ethyl acetate (3:2) as eluant. (3.07 g, 100%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue dissolved in water (50 ml)
  3. extractionThe aqueous mixture was extracted with chloroform (3×50 ml)
  4. dry with materialthe combined extracts dried (MgSO4)
  5. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-9dd41360d7db4f02a15ccf22e3a1798d
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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