HCID 7586306, compound → HCID 68565785, compound

HRID 1867587Notes

Reaction equation

HRID 1867587 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][C@H:28]([C:36](OC)=O)[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[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>[CH2:29]([C:28]1[NH:27][C:25](=[O:26])[N:24]([CH:21]2[CH2:22][CH2:23][N:18]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:19][CH2:20]2)[CH:36]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 7586306HCID 7586306, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 68565785HCID 68565785, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Diisobutylaluminum hydride (1M, 2.53 mL, 2.53 mmol) was added to a solution of methyl N-{[(1-benzylpiperidin-4-yl)amino]carbonyl}phenylalaninate (800 mg, 2.02 mmol) in toluene (7.5 mL) and dichloromethane (7.5 μL) at −78° C. and stirred for 30 min and then warmed to ambient temperature. After 5 min at room temperature, the reaction was quenched with saturated potassium sodium tartrate solution (20% solution), extracted with dichloromethane and treated with a 4 N HCl solution (50 mL). After 30 min. the mixture was extracted with water, basified to pH=7, and extracted with dichloromethane (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica gel, 0 to 8% {1% ammonium hydroxide/methanol} in methylene chloride gradient elution), gave the title compound (250 mg). MS 348.3 (M+1)

Workup

  1. waitAfter 5 min at room temperature
  2. customthe reaction was quenched with saturated potassium sodium tartrate solution (20% solution)
  3. extractionextracted with dichloromethane
  4. additiontreated with a 4 N HCl solution (50 mL)
  5. extractionAfter 30 min. the mixture was extracted with water
  6. extractionextracted with dichloromethane (3×)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification
  11. washby column chromatography (silica gel, 0 to 8% {1% ammonium hydroxide/methanol} in methylene chloride gradient elution)

Sources & evidence

ORD record
ord-e9dfb5c39a2a4a4c961f309e40239341
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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