Acetamide → 1-Aminocyclopentanemethanol
Reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].[CH2:10](CC(NC1C=CC=CC=1)=[O:14])[CH3:11].C(N)(=O)C.C([C:28]1[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=CC=1N)C.NC1C=CC=CC=1.C([C:47]1[CH:52]=[C:51]([N+]([O-])=O)[CH:50]=[CH:49][C:48]=1[N:56]=[C:57]=[S:58])C.OCCN.Cl.ClCC1(N)CCCC1>>[OH:14][CH2:6][C:4]1([NH2:5])[CH2:3][CH2:9][CH2:8][CH2:7]1.[CH2:10]([C:2]1[CH:32]=[C:33]([N+:35]([O-:37])=[O:36])[CH:34]=[CH:28][C:1]=1[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[N:5]=[C:57]1[S:58][CH2:49][C:48]2([CH2:47][CH2:52][CH2:51][CH2:50]2)[NH:56]1)[CH3:11]Participants
Reactant 8
Product 2
Procedure
2-Ethylaniline was protected as 2-ethylacetanilide according to Method A2a, Step 1. The acetamide was converted to 2-ethyl-4-nitroaniline, then deprotected according to Method A2a, Step 2. The aniline was converted to 2-ethyl-4-nitrophenyl isothiocyanate according to Method A2a, Step 3. 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 2-ethyl-4-nitrophenyl isothiocyanate according to Method C1e to give 2-(2-ethyl-4-nitrophenylphenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 2-(2-ethyl-4-nitrophenylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.
Sources & evidence
- ORD record
- ord-cb416b9fa03e4586b13517955fe64e58
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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