Pyrrolidine → HCID 23114376, compound

HRID 1787379Notes

Reaction equation

HRID 1787379 reaction equation
I[CH2:2][C:3]1([CH3:32])[CH2:7][C:6]2[C:8]([CH3:31])=[C:9]([NH:23][C:24](=[O:30])[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:10]([CH3:22])=[C:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[C:5]=2[O:4]1.[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>O>[CH:19]([C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C:11]2[C:5]3[O:4][C:3]([CH3:32])([CH2:2][N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)[CH2:7][C:6]=3[C:8]([CH3:31])=[C:9]([NH:23][C:24](=[O:30])[CH2:25][C:26]([CH3:28])([CH3:27])[CH3:29])[C:10]=2[CH3:22])=[CH:18][CH:17]=1)([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 23113976HCID 23113976, compound

Product 1

HCID 23114376HCID 23114376, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(2-(iodomethyl)-7-(4-isopropylbenzyl)-2,4,6-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (102 mg, 0.19 mmol) obtained in Example 336 and pyrrolidine (1.5 mL) was reacted using a microwave reactor (110° C., hold time 20 min, 250 W). Water was added to the reaction solution and the product was extracted with ethyl acetate. The combined organic layers were washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure to obtain 86 mg (yield: 95%) of the title compound. Melting point: 143-144° C. (THF-hexane).

Workup

  1. customwas reacted
  2. custom(110° C., hold time 20 min, 250 W)
  3. extractionthe product was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1ab015e52c94396bf1ab34fb627b562
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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