HCID 58020720, compound → N-Boc-5-Hydroxyindoline

HRID 1633674Notes

Reaction equation

HRID 1633674 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]CC3C=CC=CC=3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58020720HCID 58020720, compound

Product 1

HCID 10657398N-Boc-5-HydroxyindolineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

23 g (68.6 mmol) 5-Benzyloxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 250 ml methanol with 2.5 g 10% Pd/C were hydrogenated for 2 h, the suspension was filtered. The filtrate was concentrated and purified by column chromatography on silica gel with MeOH/EtOAc 1:1, yielding 14.4 g (90%) 5-Hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as colorless solid, MS: 235 (M).

Workup

  1. filtrationthe suspension was filtered
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography on silica gel with MeOH/EtOAc 1:1

Sources & evidence

ORD record
ord-0f4dd7523c664369832173c3e7b02b57
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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