2-Methyl-propane-2-sulfinic acid [1-benzyl-4-(2-phenyl-chroman-6-yloxy)-cyclohexyl]-amide → 1-Benzyl-4-(2-phenyl-chroman-6-yloxy)-cyclohexylamine

HRID 59782Notes

Reaction equation

[CH2:1]([C:8]1([NH:31]S(C(C)(C)C)=O)[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][CH:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:19][CH2:18]3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[CH2:1]([C:8]1([NH2:31])[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][CH:20]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:19][CH2:18]3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

120 mg of 2-methyl-propane-2-sulfinic acid [1-benzyl-4-(2-phenyl-chroman-6-yloxy)-cyclohexyl]-amide (0.23 mmol) were dissolved in 2 ml of trifluoroacetic acid in a sealed microwave tube and heated in a microwave reactor for 1 h at 130° C. The solvent was removed under reduced pressure and the resulting residue purified by reversed phase HPLC chromatography. 21 mg of 1-benzyl-4-(2-phenyl-chroman-6-yloxy)-cyclohexylamine were obtained as a solid (17%).

Workup

customThe solvent was removed under reduced pressure
customthe resulting residue purified by reversed phase HPLC chromatography

Sources & evidence

ORD record: ord-e43a372afcbb41daac7f8583c3257d2a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440941B2

Reaction notes

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