Ethanolamine → 1-Aminocyclopentanemethanol

HRID 276579Notes

Reaction equation

C[C:2]1[C:8](C)=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:10][C:11]1[C:17]([CH3:18])=[C:16]([I:19])[CH:15]=[CH:14][C:12]=1[NH2:13].NC1C=CC=CC=1.CC1[C:33]([CH3:34])=[C:32](I)[CH:31]=[CH:30][C:29]=1[N:36]=[C:37]=[S:38].[OH:39]CCN.O=S(Cl)Cl>>[NH2:4][C:3]1([CH2:2][OH:39])[CH2:5][CH2:6][CH2:7][CH2:8]1.[CH3:10][C:11]1[C:17]([CH3:18])=[C:16]([I:19])[CH:15]=[CH:14][C:12]=1[N:13]=[C:37]1[NH:36][CH2:29][C:30]2([CH2:31][CH2:32][CH2:33][CH2:34]2)[S:38]1

Participants

Reactant 6

HCID 700Ethanolamine

HCID 6115Aniline

HCID 68932,3-Dimethylaniline

HCID 24386Thionyl Chloride

HCID 140402864-Iodo-2,3-dimethylbenzenamine

HCID 18316004HCID 18316004, compound2×

Product 2

HCID 663071-Aminocyclopentanemethanol

HCID 178429778HCID 178429778, compound

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 followed by 2,3-dimethyl-4-iodophenyl isothiocyanate according to Method C2a 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 D2a to give 3-isobutyl-2-(4-iodo-2-n-propylphenylimino)-1-thia-3-azaspiro[4.4]nonane. The phenyl iodide was reacted with trimethylsilylacetylene according to Method D8a, Step 1 to give 3-isobutyl-2-(2,3-dimethyl-4-(2-trimethylsilylethynyl)phenylimino)-1-thia-3-azaspiro[4.4]nonane. The silylacetylene was deprotected according to Method D8a, Step 2 to afford 3-isobutyl-2-(2,3-dimethyl-4-ethynylphenylimino)-1-thia-3-azaspiro[4.4]nonane.

Sources & evidence

ORD record: ord-75a59c8416ce4860a0b6d69d51abccaa
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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