HCID 178501104, compound → HCID 178501103, compound

HRID 1840563Notes

Reaction equation

HRID 1840563 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][N:12]2[CH:17]=[CH:16][N:15](C(OCC3C=CC=CC=3)=O)[CH2:14][C:13]2=[O:28])[CH2:7][CH2:6]1)=[O:4]>[Pd].CO>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C:13]2=[O:28])[CH2:9][CH2:10]1)=[O:4]

Participants

4

Reactant 1

HCID 178501104HCID 178501104, compound

Product 1

HCID 178501103HCID 178501103, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(trans-4-methoxycarbonylcyclohexylmethyl)-4-benzyloxycarbonyl-2-oxo-1,2,3,4-tetrahydropyrazine (2.0 g) and 10% palladium on carbon (400 mg) in methanol (80 ml) was stirred at room temperature for 15 hours, under hydrogen atmosphere, and the catalyst was filtered off. The reaction solution was concentrated to give colorless oil of 1-(trans-4-methoxycarbonylcyclohexylmethyl)-2-piperazinone. To the obtained 1-(trans-4-methoxycarbonylcyclohexylmethyl)-2-piperazinone were added ethyl acetate (20 ml) and sodium bicarbonate solution (20 ml), and then was added 6-chloro-2-naphthanlenesulfonyl chloride (1.5 g), and the mixture was stirred at room temperature for 5 hours. The separated organic layer was washed with water and brine, dried and concentrated, and the residue was crystallized from ethyl acetate to give colorless crystals of 4-(6-chloro-2-naphthanlenesulfonyl)-1-(trans-4-methoxycarbonylcyclohexylmethyl)-2-piperazinone (1.4 g).

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-fc225bb2a8ab42439520fc8bd949946f
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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