HCID 13891111, compound → (3S,4S)-3-Hydroxy-4-amino-5-cyclohexyl-1-pentene
Reaction equation
[CH:1]1([CH2:7][C@H:8]2[CH:12]([CH:13]=[CH2:14])[O:11]C(=O)[NH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>O1CCOCC1.O>[OH:11][C@H:12]([C@@H:8]([NH2:9])[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:13]=[CH2:14]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To the resultant 5S-diastereomer from Example 4 (2.06 g, 9.84 mmol) in dioxane (180 ml) and water (120 ml) was added barium hydroxide octahydrate (6.24 g, 19.8 mmol). The mixture was refluxed for 18 h, cooled, filtered, concentrated, taken up in water and extracted with ethyl acetate which was dried over Na2SO4 and evaporated to afford 1.64 9 (91%) of the desired product, m.p.: 59°-61° C.