5-Methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-6-morpholinocarbonyloxy-1-oxaspiro[2,5]octane → 5-Methoxy-4-[2-methyl-3-(3-methylbutyl)oxiranyl]-6-morpholinocarbonyloxy-1-oxaspiro[2,5]octane
Reaction equation
[CH3:1][O:2][CH:3]1[CH:10]([O:11][C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[CH2:9][CH2:8][C:5]2([O:7][CH2:6]2)[CH:4]1[C:20]1([CH3:28])[CH:22]([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[O:21]1>C(OCC)(=O)C.[Pt]=O>[CH3:1][O:2][CH:3]1[CH:10]([O:11][C:12]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[O:13])[CH2:9][CH2:8][C:5]2([O:7][CH2:6]2)[CH:4]1[C:20]1([CH3:28])[CH:22]([CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[O:21]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-6-morpholinocarbonyloxy-1-oxaspiro[2,5]octane (1.23 g) in ethyl acetate (12 ml) was hydrogenated under hydrogen (1 atom) in the presence of platinum oxide (120 mg) for 1 hour. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel eluted with a mixture of diethyl ether and n-hexane (1:1, V/V) to give 5-methoxy-4-[2-methyl-3-(3-methylbutyl)oxiranyl]-6-morpholinocarbonyloxy-1-oxaspiro[2,5]octane (996 mg) as an oil, which was standing on to give crystals of the same compound.
Workup
- customThe catalyst was removed by filtration
- concentrationthe filtrate was concentrated in vacuo
- customThe residue was purified by column chromatography on silica gel
- washeluted with a mixture of diethyl ether and n-hexane (1:1, V/V)
Sources & evidence
- ORD record
- ord-b3ab2f4cb2874e4abdb97ba06eb3a23d
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04954496
Reaction notes
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