Methanol → 1-(2-(4-(6-Methoxy-2-(5-(methylsulfinyl)thiophen-2-yl)naphthalen-1-yloxy)phenoxy)ethyl)piperidine

HRID 445207Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:28]=[CH:27][C:17]([O:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:16][CH:15]=1)=[C:8]([C:29]1[S:30][C:31]([S:34][CH3:35])=[CH:32][CH:33]=1)[CH:7]=[CH:6]2.[O:36]1CCCC1.CO.S(O)([O-])(=O)=O.S(O)(OO)(=O)=O.[K+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:28]=[CH:27][C:17]([O:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:16][CH:15]=1)=[C:8]([C:29]1[S:30][C:31]([S:34]([CH3:35])=[O:36])=[CH:32][CH:33]=1)[CH:7]=[CH:6]2

Participants

Conditions

Temperature: 0 °C

Procedure

Add 1-(2-(4-(6-methoxy-2-(5-(methylthio)thiophen-2-yl)naphthalen-1-yloxy)phenoxy)ethyl)piperidine (84 mg, 0.17 mmol), tetrahydrofuran (3.3 mL) and methanol (3.3 mL) to a round bottom flask under nitrogen. Cool the resulting solution to 0° C. and add solution of potassium peroxymonosulfate sulfate (102 mg; 0.17 mmol) in water (1.7 mL). Stir the resulting mixture at 0° C. for 30 min. Load the mixture onto an SCX acidic ion exchange column. Flush the column with 1:1 methanol/dichloromethane and elute with 1:1 2M ammonia in methanol/dichloromethane. Concentrate the ammonia containing eluent in vacuo to give the title compound (87 mg, 0.17 mmol): mass spectrum (m/z): 522 (M+1).

Workup

customFlush the column with 1:1 methanol/dichloromethane
washelute with 1:1 2M ammonia in methanol/dichloromethane
concentrationConcentrate the ammonia containing eluent in vacuo

Sources & evidence

ORD record: ord-ff85a319f1df4f0c86f480029cdf1ec1
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476300B2

Reaction notes

Loading…