HCID 86741156, compound → HCID 754468, compound

HRID 1249086Notes

Reaction equation

HRID 1249086 reaction equation
C([N:8]1[C@@H:20]([C:21]([O:23][CH3:24])=[O:22])[CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[C@@H:9]1[CH3:25])C1C=CC=CC=1>CO.[Pd]>[CH3:25][C@H:9]1[C:10]2[NH:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[CH2:19][C@H:20]([C:21]([O:23][CH3:24])=[O:22])[NH:8]1

Participants

4

Reactant 1

HCID 86741156HCID 86741156, compound

Product 1

HCID 754468HCID 754468, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl (1RS,3SR)-trans-2-benzyl-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (14.0 g) is dissolved in methanol (600 ml), and thereto is added 10% Pd-C (1.0 g). The mixture is subjected to catalytic reduction under atmospheric pressure. After the reaction, the catalyst is removed by filtration and washed with methanol. The filtrate and the washing liquid are combined and distilled to remove the solvent. The residue is recrystallized from methanol-isopropyl ether to give the title compound (10.08 g, 98.5%) as colorless prisms, m.p. 152°-154° C.

Workup

  1. customAfter the reaction
  2. customthe catalyst is removed by filtration
  3. washwashed with methanol
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe residue is recrystallized from methanol-isopropyl ether

Sources & evidence

ORD record
ord-6d28a67fa4a142d3aa2071c4ea0200e1
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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