Ethanolamine → 1-Aminocyclopentanemethanol
Reaction equation
NC1C2C[CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([N+:12]([O-])=O)=[CH:4]C=1.[N+](C1C2C[CH2:25][CH2:24][CH2:23][C:22]=2[C:21]([N:28]=C=S)=[CH:20]C=1)([O-])=[O:16].OCCN.O=S(Cl)[Cl:37]>>[NH2:12][C:5]1([CH2:4][OH:16])[CH2:6][CH2:7][CH2:8][CH2:9]1.[ClH:37].[NH2:28][C:21]1([CH2:20][Cl:37])[CH2:22][CH2:23][CH2:24][CH2:25]1Participants
Procedure
1-Amino-5,6,7,8-tetrahydronaphthaline was converted to 1-acetamino-5,6,7,8-tetrahydronaphthaline according to Method A2a, Step 1. The acetanilide was converted to 1-acetamino-4-nitro-5,6,7,8-tetrahydronaphthaline according according to Method A2a, Step 2. The acetanilide was deprotected according to Method A2a, Step 3 to give 1-amino-4-nitro-5,6,7,8-tetrahydronaphthaline. The aniline was converted to 4-nitro-5,6,7,8-tetrahydro-1-naphthyl 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 4-nitro-5,6,7,8-tetrahydro-1-naphthyl isothiocyanate according to Method C1a to give 2-(4-nitro-5,6,7,8-tetrahydro-1-naphthylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford 1-isobutyl-2-(4-nitro-5,6,7,8-tetrahydro-1-naphthylimino)-3-thia-1-azaspiro[4.4]nonane.
Sources & evidence
- ORD record
- ord-a2574148ec1c4ad5929f8071fca1bd97
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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