HCID 57550257, compound → 7-Benzyl-2,7-diazaspiro[4.4]nonan-3-one

HRID 548630Notes

Reaction equation

HRID 548630 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:17][C:18]([O:20]C)=O)([CH2:13][N+:14]([O-])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Ni].O.C(O)C>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]2([CH2:13][NH:14][C:18](=[O:20])[CH2:17]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 57550257HCID 57550257, compound

Product 1

HCID 574169747-Benzyl-2,7-diazaspiro[4.4]nonan-3-oneYield 60%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

A suspension of methyl [1-benzyl-3-(nitromethyl)pyrrolidin-3-yl]acetate a46 (3.3 g, 1.1 mmol, 1 eq) and Raney nickel (1 g of a 50% slurry in water) in ethanol (200 ml) is shaken in a Parr bottle at 30° C. for 24 h, under a hydrogen pressure of 40 psi. The reaction mixture is then filtered through Celite and the filtrate is concentrated to afford 1.8 g of 7-benzyl-2,7-diazaspiro[4.4]nonan-3-one a47 as a brown oil.

Workup

  1. filtrationThe reaction mixture is then filtered through Celite
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-7304eecbb2904fa98e2a3431d5f7727c
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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