Reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH3:9][C@:10]12[CH2:27][CH2:26][C@H:25]3[C@@H:15]([CH2:16][CH2:17][C@@H:18]4[C@:23]3([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]4)[C@@H:14]1[CH2:13][CH2:12][C:11]2=O.C([BH3-])#N.[Na+].[OH-].[Na+]>O1CCCC1.C(O)(=O)C.CO>[CH3:9][C@:10]12[CH2:27][CH2:26][C@H:25]3[C@@H:15]([CH2:16][CH2:17][C@@H:18]4[C@:23]3([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19]4)[C@@H:14]1[CH2:13][CH2:12][C@@H:11]2[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][NH2:8]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
A 100 ml round-bottomed flask, equipped with a magnetic stir bar, condenser, and nitrogen inlet tube, was charged with 1,6-hexanediamine (0.904 g) and 15 ml of methanol. The solution was treated with glacial acetic acid until the pH was 6.7. To this mixture was added 15 ml of tetrahydrofuran, 5α-androstan-17-one (0.704 g) and sodium cyanoborohydride (0.228 g). The mixture was heated to reflux for 18 h. After cooling, the solution was made basic with aqueous 2M sodium hydroxide to a pH of 13-14. The solution was extracted with chloroform (3×) and the combined organic layers were washed with water and brine, dried (Na2SO4), filtered, and concentrated to give 1.2 g of an oil.
Workup
- customA 100 ml round-bottomed flask, equipped with a magnetic stir bar, condenser, and nitrogen inlet tube
- temperatureThe mixture was heated
- temperatureto reflux for 18 h
- temperatureAfter cooling
- extractionThe solution was extracted with chloroform (3×)
- washthe combined organic layers were washed with water and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-789156abb9c240ff9950dea785b16ca3
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05196542
Linked notes
Loading…