Pyrrolidine → HCID 19078604, compound

HRID 964799Notes

Reaction equation

HRID 964799 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-943d75b6456b4deeb99c0957698eb56d
Source dataset
uspto-grants-1998_06
Patent number
US05770772

Reaction notes

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