4-Aminocyclohexanol → HCID 11610264, compound

HRID 2421945Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

2-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.15 g, 0.53 mmol), 4-aminocyclohexanol (0.092 g, 0.80 mmol) and TEA (0.081 g, 0.80 mmol) was dissolved in dry MeCN (3 ml). The reaction was heated in a microwave reactor at 120° C. for 10 mins. A few extra drops of 4-aminocyclohexanol was added and the reaction was heated in a microwave reactor at 140° C. for 20 mins. The residue was purified by silica gel column chromatography using a 25:75 mixture of hexane and EtOAc, to give a 50:50 mixture of cis and trans isomers (0.130 g, 67%). The mixture was separated by HPLC (C8, 0.05M NH4OAc (pH=4.1):MeCN 1:1) to give cis (Example 38) and trans (Example 48) isomers.

Workup

temperaturethe reaction was heated in a microwave reactor at 140° C. for 20 mins
customThe residue was purified by silica gel column chromatography
additiona 25:75 mixture of hexane and EtOAc
customto give
additiona 50:50 mixture of cis and trans isomers (0.130 g, 67%)
customThe mixture was separated by HPLC (C8, 0.05M NH4OAc (pH=4.1):MeCN 1:1)
customto give cis (Example 38) and trans (Example 48) isomers

Sources & evidence

ORD record: ord-4b38bb12255443c7bef83290cba86cd4
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960380B2

Reaction notes

Loading…