Water → HCID 178453976, compound

HRID 722020Notes

Reaction equation

HRID 722020 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[C:12]([O:16][C:17]([NH:19][C@H:20]1[CH2:25]C[C@H](N)[CH2:22][CH2:21]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C([N:29]([CH2:32][CH3:33])[CH2:30]C)C.[OH2:34]>>[C:12]([O:16][C:17]([NH:19][C@H:20]1[CH2:25][CH2:33][C@H:32]([N:29]2[CH2:30][C:6]3[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=3)[C:7]2=[O:34])[CH2:22][CH2:21]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 6212ChloroformHCID 8471TriethylamineHCID 178419079HCID 178419079, compound

Product 1

HCID 178453976HCID 178453976, compound

Conditions

Temperature
100 °C

Procedure

15 ml of toluene-1.5 ml of chloroform solution containing 500 mg of N-tert-butoxycarbonyl-trans-1,4-cyclohexanediamine, 623 mg of ethyl 2-bromomethyl benzoate and 354 mg of triethylamine was heated at 100° C. for 5 hours. After cooling, water was added to the mixture and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography to obtain 400 mg of N-tert-butoxycarbonyl-trans-4-(1-oxo-2-isoindolinyl)cyclohexylamine.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-2c0a7e42af8a4b139ebfdddec95be63c
Source dataset
uspto-grants-2006_11
Patent number
US07138397B2

Reaction notes

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