Sodium Carbonate → (3R)-2-[(benzyloxy)carbonyl]-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

HRID 373112

Reaction equation

HRID 373112 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][C@H:3]([C:14]([OH:16])=[O:15])[NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>O>[C:24]([N:2]1[C@@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:1]1)([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 675102D-1,2,3,4-Tetrahydronorharman-3-carboxylic acid

Product 1

HCID 13863913(3R)-2-[(benzyloxy)carbonyl]-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.00 g (3R)-1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]-indole-3-carboxylic acid is suspended in 50 ml water/50 ml tetrahydrofuran and 5.15 g sodium carbonate is added. The mixture is stirred for 5 minutes and 3.94 g benzyl chloroformate is added and the mixture stirred overnight. The mixture is evaporated in vacuo to remove the THF, the aqueous residue acidified with 1N hydrochloric acid and the resulting solid extracted into ethyl acetate. The organic solution is washed with 1N HCl, water, brine, and dried over sodium sulfate. The solution is filtered, evaporated and the residue crystallized from toluene to give (3R)-2-carbobenzoxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid, m.p. 181°-184° C.

Workup

  1. stirringthe mixture stirred overnight
  2. customThe mixture is evaporated in vacuo
  3. customto remove the THF
  4. extractionthe resulting solid extracted into ethyl acetate
  5. washThe organic solution is washed with 1N HCl, water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution is filtered
  8. customevaporated
  9. customthe residue crystallized from toluene

Sources & evidence

ORD record
ord-a56da113337748c6a343aabaf1aa0260
Source dataset
uspto-grants-1992_11
Patent number
US05162336

Linked notes

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