Ethanolamine → 1-Aminocyclopentanemethanol
Reaction equation
C([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])(C)C.I[C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[C:14](C(C)C)[CH:13]=1.NC1C=CC=CC=1.IC1C=CC(N=C=S)=C(C(C)C)C=1.[OH:42]CCN.O=S(Cl)[Cl:48]>>[NH2:6][C:5]1([CH2:4][OH:42])[CH2:7][CH2:8][CH2:9][CH2:10]1.[ClH:48].[NH2:16][C:15]1([CH2:14][Cl:48])[CH2:13][CH2:12][CH2:18][CH2:17]1Participants
Reactant 6
Product 2
Procedure
2-Isopropylaniline was converted to 4-iodo-2-isopropylaniline according to Method A5a. The aniline was converted to 4-iodo-2-isopropylphenyl isothiocyanate according to Method A2b. 1-Amino-1-(hydroxymethyl)cyclopentane was synthesized as described in Method B1c. The 2-hydroxyethylamine was reacted with SOCl2 according to Method B7a to give 1-amino-1-(chloromethyl)cyclopentane HCl salt. The 2-chloroethylamine was reacted with 4-iodo-2-isopropylphenyl isothiocyanate according to Method C1a to give 2-(4-iodo-2-isopropylphenylimino)-1-thia-3-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 3-cyclopentyl-2-(4-iodo-2-isopropylphenylimino)-1-thia-3-azaspiro[4.4]nonane. The phenyl iodide was reacted with CuCN according to Method D7a to afford 3-cyclopentyl-2-(4-cyano-2-isopropylphenylimino)-1-thia-3-azaspiro[4.4]nonane.
Sources & evidence
- ORD record
- ord-56f12645dd15488a846da3749f68fbb3
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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