Benzoic Acid → HCID 86755358, compound

HRID 1106506Notes

Reaction equation

HRID 1106506 reaction equation
[CH2:1]1[C@H:13]2[C@H:5]([NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=32)[CH2:4][CH2:3][N:2]1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:19](O)(=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.S1C=CC=C1.[H][H]>CO.[Pd]>[C:20]1([CH2:19][N:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C@H:13]3[CH2:1][N:2]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:3][CH2:4][C@@H:5]23)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 8030ThiopheneHCID 44593836HCID 44593836, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86755358HCID 86755358, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate 1 (22.46 g), benzoic acid (11.8 g) and thiophene (4%, 2 ml) in methanol (440 ml) was hydrogenated with palladium-on-carbon (10%, 3 g) as a catalyst. After uptake of hydrogen (1 equivalent), the catalyst was filtered off. The filtrate was evaporated, yielding 30 g (99%) of (±)-ethyl cis-1,3,4,4a,5,9b-hexahydro-5-(phenylmethyl)-2H-pyrido[4,3-b]indole-2-carboxylate (intermediate 2).

Workup

  1. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-2260fd684bbc471fa0f67d8ffdb59799
Source dataset
uspto-grants-2000_05
Patent number
US06057325

Reaction notes

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