HCID 70981496, compound → HCID 70982680, compound

HRID 1475449Notes

Reaction equation

HRID 1475449 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([CH:17]([OH:21])[CH:18]([CH3:20])[CH3:19])[N:13]=[CH:12][C:11]=2[C:10]([CH3:23])([CH3:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[O-2].[Mn+4].[O-2].C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([C:17](=[O:21])[CH:18]([CH3:19])[CH3:20])[N:13]=[CH:12][C:11]=2[C:10]([CH3:22])([CH3:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 70981496HCID 70981496, compound

Product 1

HCID 70982680HCID 70982680, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 6-(1-hydroxy-2-methyl-propyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.366 g, 1.14 mmol), DCM (50 mL) and manganese (IV) oxide (9.6 g, 110 mmol) was stirred at 20° C. for 18 h, then solids were removed by filtration and the filtrate evaporated in vacuo to give a solid. Chromatography (SiO2; gradient elution with 0-40% EtOAc in 40-60 petroleum ether) gave the title compound (0.299 g) as a colourless solid. MS: [M+H]+=319.

Workup

  1. customsolids were removed by filtration
  2. customthe filtrate evaporated in vacuo
  3. customto give a solid
  4. washChromatography (SiO2; gradient elution with 0-40% EtOAc in 40-60 petroleum ether)

Sources & evidence

ORD record
ord-3cc3a61ac9c147f4833dc6f1c9d03540
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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