Ethanolamine → 1-Aminocyclopentanemethanol
Reaction equation
C[C:2]1[C:8](C)=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C[C:11]1[C:17](C)=[C:16](I)[CH:15]=[CH:14][C:12]=1[NH2:13].NC1C=CC=CC=1.CC1C(C)=C(I)C=CC=1N=C=S.[OH:39]CCN.O=S(Cl)[Cl:45]>>[NH2:4][C:3]1([CH2:2][OH:39])[CH2:5][CH2:6][CH2:7][CH2:8]1.[ClH:45].[NH2:13][C:12]1([CH2:11][Cl:45])[CH2:14][CH2:15][CH2:16][CH2:17]1Participants
Procedure
2,3-Dimethylaniline was converted to 2,3-dimethyl-4-iodoaniline according to Method A5a. The aniline was converted to 2,3-dimethyl-4-iodophenyl isothiocyanate according to Method A2a, Step 3. 1-Amino-1-(hydroxymethyl)cyclopentane was synthesized as described in Method B1c. The 2-hydroxyethylamine was reacted with SOCl2 according to Method B7e to give 1-amino-1-(chloromethyl)cyclopentane HCl salt. The 2-chloroethylamine was reacted with 2,3-dimethyl-4-iodophenyl isothiocyanate according to Method C1e to give 2-(2,3-dimethyl-4-iodophenylimino)-1-thia-3-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2h to give 3-isobutyl-2-(4-iodo-2-n-propylphenylimino)-1-thia-3-azaspiro[4.4]nonane. The phenyl iodide was reacted with CuCN according to Method D7a to afford 3-isobutyl-2-(2,3-dimethyl-4-cyanophenylimino)-1-thia-3-azaspiro[4.4]nonane.
Sources & evidence
- ORD record
- ord-dc7f3522d4e1476cb564925bcafcee4f
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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