HCID 11567437, compound → HCID 11618213, compound

HRID 1261652Notes

Reaction equation

HRID 1261652 reaction equation
[CH:1]([C@:4]1([C:16]([N:18]2[CH2:23][CH:22]=[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[O:17])[CH2:8][CH2:7][C@@H:6]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:5]1)([CH3:3])[CH3:2]>CO.[Pd]>[CH:1]([C@:4]1([C:16]([N:18]2[CH2:19][CH2:20][CH:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:22][CH2:23]2)=[O:17])[CH2:8][CH2:7][C@@H:6]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 11567437HCID 11567437, compound

Product 1

HCID 11618213HCID 11618213, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-{(1R,3S)-3-isopropyl-3-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]cyclopentyl}tetrahydro-2H-pyran-4-amine (22 mg, 0.055 mmol) in methanol (2.0 mL) under N2 was added palladium (10 mg) (10% dry weight on wet activated carbon). The reaction mixture was stirred at room temperature under H2 (1 atm) overnight (22 h) and filtered through celite. The celite was washed with methylene chloride and the filtrate was concentrated to give 20 mg of desired product after lyophilization. MS calculated for C25H38N2O2: (M+H) 399; found 399.2.

Workup

  1. filtrationfiltered through celite
  2. washThe celite was washed with methylene chloride
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7830ad6ddf6443ac9956b2fe46ba187d
Source dataset
uspto-grants-2013_06
Patent number
US08470827B2

Reaction notes

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