Pyrrolidine → HCID 19078604, compound

HRID 234260Notes

Reaction equation

HRID 234260 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:7][C:8]1([CH3:23])[CH2:12][C:11]2[C:13]([CH3:22])=[C:14]([NH:19]C=O)[C:15]([CH3:18])=[C:16]([CH3:17])[C:10]=2[O:9]1>O>[NH2:19][C:14]1[C:15]([CH3:18])=[C:16]([CH3:17])[C:10]2[O:9][C:8]([CH3:7])([CH2:23][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:12][C:11]=2[C:13]=1[CH3:22]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 10495279HCID 10495279, compound

Product 1

HCID 19078604HCID 19078604, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

Pyrrolidine (20 ml) was added to 2-bromomethyl-5-formylamino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (3.0 g, 9.6 mmol) and the mixture was heated at 160° C. in an autoclave for 15 hours. After the reaction mixture was cooled, the mixture was diluted with water and the product was extracted with ethylacetate. The extract was washed with water and dried and then the solvent was distilled off. The residue was purified by column chromatography on silica gel (chloroform-methanol, 9:1) and recrystallized from hexane to obtain the desired compound (2.2 g, yield: 83.5%), m.p. 85°-86° C. (dec.).

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. extractionthe product was extracted with ethylacetate
  3. washThe extract was washed with water
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography on silica gel (chloroform-methanol, 9:1)
  7. customrecrystallized from hexane

Sources & evidence

ORD record
ord-1cf53c9e5ecd44c09b4f57afe4168460
Source dataset
uspto-grants-1997_01
Patent number
US05594154

Reaction notes

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