Tetrahydro-4H-pyran-4-one → [2-(Tert-butyl-dimethylsilanyloxy)-ethyl]-(tetrahydro-pyran-4-yl)-amine
Reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[Si:8]([O:15][CH2:16][CH2:17][NH2:18])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]>CO>[Si:8]([O:15][CH2:16][CH2:17][NH:18][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)([C:11]([CH3:13])([CH3:14])[CH3:12])([CH3:10])[CH3:9]Participants
Procedure
To a stirred cooled solution of tetrahydro-pyran-4-one (2 g, 19.98 mmol) in methanol (30 mL) were added 2-(tert-butyl-dimethylsilanyloxy)-ethylamine (8c) (2.5 mg, 13.98 mmol). Stirring was continued for 1 h at room temperature. The reaction mixture was cooled and Na(CN)BH3 (2.5 g, 39.96 mmol) was added portion-wise, followed by stirring at room temperature for 20 h. The reaction mixture was quenched with water and the methanol was removed. The mixture was subsequently extracted with dichloromethane (3×30 mL) and the organic part was concentrated, dried and purified by Combi-Flash column (eluted at 20-50% ethyl acetate in hexane) to get [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-(tetrahydro-pyran-4-yl)-amine (8j) (2.5 g, 48.23 mmol) as a light yellow oil.
Workup
- temperatureThe reaction mixture was cooled
- stirringby stirring at room temperature for 20 h
- customThe reaction mixture was quenched with water
- customthe methanol was removed
- extractionThe mixture was subsequently extracted with dichloromethane (3×30 mL)
- concentrationthe organic part was concentrated
- customdried
- custompurified by Combi-Flash column (eluted at 20-50% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-fdbe61d4fa7c432a88d888bbf5d61ccc
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045486B2
Reaction notes
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