Formylcycloheptane → N-[1-(Cycloheptylmethyl)piperidin-4-yl]-2-cyclopentyl-2-hydroxy-2-phenylacetamide

HRID 1289812Notes

Reaction equation

HRID 1289812 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:22])[C:9]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)([OH:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.[CH:23]1([CH:30]=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.C(O)(=O)C>[CH:23]1([CH2:30][N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:22])[C:9]([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21]3)([OH:16])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:5][CH2:6]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 77961FormylcycloheptaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10662143N-(piperidin-4-yl)-2-cyclopentyl-2-hydroxy-2-phenylacetamide

Product 1

HCID 10835518N-[1-(Cycloheptylmethyl)piperidin-4-yl]-2-cyclopentyl-2-hydroxy-2-phenylacetamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

34 mg of N-(piperidin-4-yl)-2-cyclopentyl-2-hydroxy-2-phenylacetamide obtained in Step 2 of Example 27, 50 mg of cycloheptanecarbaldehyde and 10 mg of acetic acid were dissolved in tetrahydrofuran. 70 mg of sodium triacetoxyborohydride was added thereto and the resulting mixture was stirred for 17 hours. After the addition of a saturated aqueous solution of sodium bicarbonate, the reaction mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by preparative thin layer chromatography (Kieselgel™, 60F254, Art 5744 (manufactured by E. Merck; developing solvent: chloroform/methanol=10/1) to obtain the title compound.

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by preparative thin layer chromatography (Kieselgel™, 60F254, Art 5744 (manufactured by E. Merck; developing solvent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-eb7e7b4f620d4dc0b86fb8239145764a
Source dataset
uspto-grants-1998_05
Patent number
US05750540

Reaction notes

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