Ethanolamine → 1-Aminocyclopentanemethanol
Reaction equation
C([C:4]1[CH:10]=[C:9]([N+]([O-])=O)[CH:8]=[CH:7][C:5]=1[NH2:6])(C)C.C([C:17]1[CH:22]=[C:21]([N+]([O-])=[O:24])[CH:20]=[CH:19][C:18]=1[N:26]=C=S)(C)C.OCCN.O=S(Cl)[Cl:35]>>[NH2:6][C:5]1([CH2:4][OH:24])[CH2:7][CH2:8][CH2:9][CH2:10]1.[ClH:35].[NH2:26][C:18]1([CH2:17][Cl:35])[CH2:19][CH2:20][CH2:21][CH2:22]1Participants
Procedure
2-Isoropylaniline was converted to 2-isopropylacetanilide according to Method A2a, Step 1. The acetanilide was converted to 2-isopropyl-4-nitroacetanilide according to Method A2a, Step 2. The acetanilide was deprotected according to Method A2a, Step 3 to give 2-isopropyl-4-nitroaniline. The aniline was converted to 2-isopropyl-4-nitrophenyl 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 B7a to give 1-amino-1-(chloromethyl)cyclopentane HCl salt. The 2-chloroethylamine was reacted with 2-isopropyl-4-nitrophenyl isothiocyanate according to Method C1a to give 2-(2-isopropyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford 1-isobutyl-2-(2-isopropyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane.
Sources & evidence
- ORD record
- ord-6f646201a7474806b079bfe33b953da4
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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