Ethanolamine → 1-Aminocyclopentanemethanol
Reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[C:3]=1[CH3:10].I[C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[S:20])=[C:14](C)[C:13]=1C.[OH:23]CCN.O=S(Cl)Cl>>[OH:23][CH2:4][C:5]1([NH2:6])[CH2:3][CH2:2][CH2:8][CH2:7]1.[I:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[C:19]2[S:20][CH2:14][C:15]3([CH2:13][CH2:12][CH2:17][CH2:16]3)[NH:18]2)=[C:4]([CH3:9])[C:3]=1[CH3:10]Participants
6
Procedure
4-Iodo-2,3-dimethylaniline was converted to 4-iodo-2,3-dimethylphenyl isothiocyanate according to Method A2b. 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was sequentially reacted with SOCl2 and 4-iodo-2,3-dimethylphenyl isothiocyanate according to Method C2a to give 2-(4-iodo-2,3-dimethylphenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 2-(4-iodo-2,3-dimethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane. The phenyl iodide was reacted with CuCN according to Method D7a to afford 2-(4-cyano-2,3-dimethylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.
Sources & evidence
- ORD record
- ord-88f9f742aede407c8312263a0a6f6c0e
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
Loading…