1-Aminocyclopentanemethanol → HCID 178439353, compound
Reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH2:9][CH2:10][CH3:11])[CH:3]=1.IC1C=[CH:17][C:16]([N:19]=[C:20]=[S:21])=[C:15]([CH2:22][CH2:23][CH3:24])C=1.NC1(CO)CCCC1.[N-]=C=S>>[I:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[C:20]2[S:21][CH2:17][C:16]3([CH2:15][CH2:22][CH2:23][CH2:24]3)[NH:19]2)=[C:4]([CH2:9][CH2:10][CH3:11])[CH:3]=1Participants
Procedure
4-Iodo-2-n-propylaniline was converted into 4-iodo-2-n-propylphenyl isothiocyanate in a manner analogous to Method A2b. Concurrently, 1-amino-1-(hydroxymethyl)cyclopentane was converted to the chloromethyl analogue, then reacted with the isothiocyanate in a manner analogous to Method C2a to give 2-(4-iodo-2-propylphenylimino)-3-thia-1-azaspiro[4.4]nonane. A slurry of 2-(4-iodo-2-propylphenylimino)-3-thia-1-azaspiro[4.4]nonane (0.54 g, 1.35 mmol) and CuCN (0.24 g, 2.70 mmol) in DMF (4 mL) was heated at 140° C. overnight. The resulting mixture was cooled to room temp, concentrated under reduced pressure and purified by flash chromatography (10% EtOAc/hex) to give 2-(4-cyano-2-propylphenylimino)-3-thia-1-azaspiro[4.4]nonane as a white solid (0.26 g, 65%): TLC (30% EtOAc/hex) Rf0.37.
Sources & evidence
- ORD record
- ord-03656c654a814341b36dd661d39ba534
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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