HCID 54218676, compound → HCID 54374078, compound

HRID 2287472Notes

Reaction equation

HRID 2287472 reaction equation
[C:1]([NH:9][C@@H:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=2)[CH2:12][C@H:11]1[O:22][C:23](=[O:25])[CH3:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.O=[Pt]=O>[C:1]([NH:9][C@@H:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=2)[CH2:12][C@H:11]1[O:22][C:23](=[O:25])[CH3:24])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 54218676HCID 54218676, compound

Product 1

HCID 54374078HCID 54374078, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of trans-1-benzamido-2-acetoxy-6-nitroindane (one part), prepared as described in Preparation 2, in EtOAc is treated with H2 (60 psi) in the presence of PtO2 for several hours. The catalyst is removed and the solvent evaporated to give trans-1-benzamido-2-acetoxy-6-aminoindane. A solution of this aminoindane (1 part) in a mixture of pyridine (16 parts), 4-dimethylaminopyridine (0.15 parts), and CH2Cl2 is treated with a solution of an aroyl (RCOCl) chloride (1.2 parts) and the reaction stirred over night. The reaction is poured into ice-water, the organic layer separated and consecutively washed with saturated aqueous sodium bicarbonate and brine. The organics are dried and the solvent evaporated to give trans-1-benzamido-2-acetoxy-6-carboxamino-indane. A solution of this indane in 1 M NaOH in methanol was stirred over night. The reaction is poured into ice-water and extracted with CH2Cl2. The organic extracts are washed with brine, dried, and the solvent evaporated to give the trans-1-benzamido-2-hydroxy-6-carboxamnido-indane.

Workup

  1. customThe catalyst is removed
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-e59ec12a2d73433eaebe7484db79380d
Source dataset
uspto-grants-2000_07
Patent number
US06083986

Reaction notes

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