HCID 54231958, compound → HCID 56977973, compound

HRID 1266465Notes

Reaction equation

HRID 1266465 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][N:8]([C:11](=[O:13])[CH3:12])[CH:7]1[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)=[O:5])[CH3:2]>[Pd].C(O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][N:8]([C:11](=[O:13])[CH3:12])[CH:7]1[C:14]1[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 54231958HCID 54231958, compound

Product 1

HCID 56977973HCID 56977973, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred mixture of 1-acetyl-2-(4-nitro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (3 g, Reference Example 20) and 10% palladium on charcoal in ethanol (150 mL) was hydrogenated under atmospheric pressure for 4 hours at room temperature and then filtered through a celite pad. The filter pad was washed with ethanol (50 mL) and the combined filtrate plus washings were evaporated. The residue was subjected to flash chromatography on silica (330 g, 20-451 μm, 0.6 bar) eluting with a mixture of dichloromethane and methanol (95:5, v/v). The fractions containing the compound of RF 16/63 (thin layer chromatography plate ref. #05719, Merck KGaA, 64271 Darmstatd, Germany, dichloromethane:methanol, 95:5, v/v) were pooled and evaporated under reduced pressure (2.7 kPa) to give the title compound (1.71 g).

Workup

  1. filtrationfiltered through a celite pad
  2. washThe filter pad was washed with ethanol (50 mL)
  3. customthe combined filtrate plus washings were evaporated
  4. washeluting with a mixture of dichloromethane and methanol (95:5
  5. additionThe fractions containing the compound of RF 16/63 (thin layer chromatography plate ref
  6. customevaporated under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-01667025f92d427796caaa966e457179
Source dataset
uspto-grants-2003_04
Patent number
US06548533B2

Reaction notes

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