Diisobutylaluminumhydride → HCID 68563758, compound

HRID 1867586Notes

Reaction equation

HRID 1867586 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:25]([NH:27][CH:28]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[C:29](OC)=O)=[O:26])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.ClCCl>[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([N:24]2[CH:29]=[C:28]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[NH:27][C:25]2=[O:26])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86620349HCID 86620349, compound

Product 1

HCID 68563758HCID 68563758, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Diisobutylaluminum hydride (1 M, 1.18 mL, 1.18 mmol) was added to a solution of methyl ({[(1-benzylpiperidin-4-yl)amino]carbonyl}amino)(4-fluorophenyl)acetate (430 mg, 1.08 mmol) in toluene (5 mL) and dichloromethane (5 mL) at −78° C. and stirred for 30 min and then warmed to 0° C. After 20 min at 0° C., the reaction was quenched with 1 N saturated potassium sodium tartrate solution (20 mL) and the mixture was extracted with ethyl acetate (2×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The crude material was treated with 4 N HCl in dioxane (4 mL), and stirred for 5 min. The mixture was concentrated, dissolved in dichloromethane and extracted with saturated sodium bicarbonate (2×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica gel, 0 to 7% {1% ammonium hydroxide/methanol} in methylene chloride gradient elution), gave the title compound (150 mg). MS 400.29 (M+1)

Workup

  1. waitAfter 20 min at 0° C.
  2. customthe reaction was quenched with 1 N saturated potassium sodium tartrate solution (20 mL)
  3. extractionthe mixture was extracted with ethyl acetate (2×)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionThe crude material was treated with 4 N HCl in dioxane (4 mL)
  8. stirringstirred for 5 min
  9. concentrationThe mixture was concentrated
  10. dissolutiondissolved in dichloromethane
  11. extractionextracted with saturated sodium bicarbonate (2×)
  12. dry with materialThe combined organic extracts were dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customPurification
  16. washby column chromatography (silica gel, 0 to 7% {1% ammonium hydroxide/methanol} in methylene chloride gradient elution)

Sources & evidence

ORD record
ord-d69e6e2afb1d44dea30dadc93a3b8d87
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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