Methanol → 3-(1-Nitrocylopentyl) propionaldehyde dimethyl acetal

HRID 2226412Notes

Reaction equation

HRID 2226412 reaction equation
[N+:1]([C:4]1([CH2:9][CH2:10][CH:11]=[O:12])[CH2:8][CH2:7][CH2:6][CH2:5]1)([O-:3])=[O:2].[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:24][OH:25]>>[CH3:24][O:25][CH:11]([O:12][CH3:13])[CH2:10][CH2:9][C:4]1([N+:1]([O-:3])=[O:2])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 136797083-(1-Nitrocyclopentyl)propionaldehyde

Product 1

HCID 231721213-(1-Nitrocylopentyl) propionaldehyde dimethyl acetal

Procedure

Condense nitrocyclopentane (prepared from bromocyclopentane and sodium nitrite) and acrolein in tetrahydrofuran in the presence of sodium hydride to obtain 3-(1-nitrocyclopentyl)propionaldehyde. Treat this aldehyde with p-toluenesulfonic acid in methanol and isolate 3-(1-nitrocylopentyl) propionaldehyde dimethyl acetal. Hydrogenate this compound with Raney nickel. Isolate 3-(1-aminocyclopentyl)propionaldehyde dimethylacetal and dissolve in aqueous acetone in the presence of p-toluenesulfonic acid and heat under reflux, followed by addition of toluene and azeotrope the mixture to give 1-azaspiro[4.4]-Δ1 -nonane.

Sources & evidence

ORD record
ord-ad8b22dc60944475a02dee144c37df5f
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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