Ethanolamine → 1-Aminocyclopentanemethanol
Reaction equation
[OH:1][CH2:2][CH2:3][NH2:4].Cl.Cl[CH2:7][C:8]1([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9]1.[C:14]([C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[S:24])=[C:18]([CH2:25][CH3:26])[CH:17]=1)#[N:15]>>[OH:1][CH2:2][C:3]1([NH2:4])[CH2:10][CH2:9][CH2:8][CH2:7]1.[C:14]([C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]2[S:24][CH2:7][C:8]3([CH2:12][CH2:11][CH2:10][CH2:9]3)[NH:13]2)=[C:18]([CH2:25][CH3:26])[CH:17]=1)#[N:15]Participants
Procedure
1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was converted to 1-chloromethylcyclopentanamine HCl salt according to Method B7e. 1-Chloromethylcyclopentanamine HCl salt was reacted with 4-cyano-2-ethylphenyl isothiocyanate according to Method C1e to give 2-(4-cyano-2-ethylphenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 2-(4-cyano-2-ethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane. The nitrile was hydrolyzed according to Method D9a to give 2-(4-carboxy-2-ethylphenylimino)-1-2-cyclopentyl-3-thia-1-azaspiro[4.4]nonane. The benzoic acid was reacted with dimethylamine according to Method D6b to afford 2-(4-(N,N-dimethylcarbamoly)-2-ethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.
Sources & evidence
- ORD record
- ord-5e84c47644bb4b429684786b02dc99d2
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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