4-Aminocyclohexanol → HCID 11717819, compound

HRID 2422056Notes

Reaction equation

[CH2:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4].[NH2:20][CH:21]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]1>>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:20][CH:21]2[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 812934-Aminocyclohexanol

HCID 672426232-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 11717819HCID 11717819, compound

Procedure

The title compound was prepared from 2-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide and 4-aminocyclohexanol in a similar manner as described for e.g. Example 6 and 7 affording a mixture of cis and trans isomeres. 1H NMR (500 MHz, CD3CN): δ 0.61-0.72 (m, 2H), 0.95-0.99 (m, 6H), 1.02-1.10 (m, 2H), 1.17-1.27 (m, 2H), 1.38-1.60 (m, 12H), 1.64-1.80 (m, 8H), 2.46 (d, 1H), 2.55 (d, 1H), 2.86-3.05 (m, 2H), 3.29-3.38 (m, 1H), 3.60-3.69 (m, 5H), 5.55-5.66 (m, 2H), 7.47-7.57 (m, 10H).

Workup

additiona mixture of cis and trans

Sources & evidence

ORD record: ord-da7e645d95864994b978311ccfe475d8
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960380B2

Reaction notes

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