Nitrogen → (6R)-6-Cyclohexyl-2-piperazinone

HRID 579161Notes

Reaction equation

HRID 579161 reaction equation
COC(=O)[CH2:4][NH:5][CH2:6][C@H:7]([NH:14][C:15]([O:17]CC1C=CC=CC=1)=O)[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.N#N>CO.C(Cl)Cl.[Pd]>[CH:8]1([C@H:7]2[NH:14][C:15](=[O:17])[CH2:4][NH:5][CH2:6]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 2

HCID 947NitrogenHCID 66684479HCID 66684479, compound

Product 1

HCID 66684779(6R)-6-Cyclohexyl-2-piperazinoneYield 128.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a 2.0 L round bottom flask containing a solution of ((R)-2-Benzyloxycarbonylamino-2-cyclohexyl-ethylamino)-acetic acid methyl ester (27 g, 77 mmol) in MeOH (300 mL) under a stream of N2 was added Pd (10% on carbon, 4.1 g, 0.05 equiv). The mixture was stirred under 1.0 atm of H2 for 18 hours. The mixture was diluted with 100 mL of CH2Cl2 and filtered through Celite. The filtrate was concentrated to give crude product (R)-6-Cyclohexyl-piperazin-2-one 18 g (127%). The product, which contained impurity and solvent, was continued to the next step with no further purification.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4e1aabc2d0a241b5b1c5dad4c6e0015f
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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