HCID 58017207, compound → HCID 58017226, compound

HRID 661579Notes

Reaction equation

HRID 661579 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH:16]([C:18]2[S:19][C:20]([Cl:24])=[C:21]([Cl:23])[CH:22]=2)[OH:17])([CH2:13][CH2:14][CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:16]([C:18]2[S:19][C:20]([Cl:24])=[C:21]([Cl:23])[CH:22]=2)=[O:17])([CH2:13][CH2:14][CH3:15])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 58017207HCID 58017207, compound

Product 1

HCID 58017226HCID 58017226, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-[(4,5-dichloro-thiophen-2-yl)-hydroxy-methyl]-3-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.423 g, 1.07 mmoles) and manganese (IV) oxide (1.3 g, 12.7 mmoles) in toluene (20 ml) was refluxed for 2 hours and filtered through a celite pad. The filtrate was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10% ethyl acetate in hexane) to yield 3-(4,5-dichloro-thiophene-2-carbonyl)-3-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester as pale yellow solid (0.27 g, 64%). M+Na: 414.

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationfiltered through a celite pad
  3. washThe filtrate was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b36f9e72f0ed490e97fb9c6a6ccd57bd
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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