Sodium Hydroxide → 6-(Methylamino)hexan-1-ol
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=O)OC(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[CH3:9][NH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
Intermediate 20 (2.14 mmol) was added to a stirring solution at 0° C. containing 95% LAH (0.426 g, 10.68 mmol) in 10 mL of anhydrous THF. This mixture was then heated to 80° C. and allowed to reflux for 3 h. After 3 h the reaction was cooled to 0° C. and water (0.426 mL), 20% (w/v) NaOH (0.426 mL), and water (1.215 mL) were added sequentially. This was stirred for 15 min at rt then MgSO4 was added and stirred for another 30 min. The mixture was filtered through celite, washed with THF, and concentrated to give the title compound. The compound was used with no further purification. ES/MS calcd. for C7H18NO+ 132.1. Found m/z=132 (M+H)+.
Workup
- temperatureto reflux for 3 h
- temperatureAfter 3 h the reaction was cooled to 0° C.
- stirringstirred for another 30 min
- filtrationThe mixture was filtered through celite
- washwashed with THF
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f9ec506eb84e4d2bad606baedbe4d8f7
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394829B2
Reaction notes
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