1,4-Dioxane → (2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7869Notes

Reaction equation

HRID 7869 reaction equation
[CH2:1]([CH:4]1[C:16](=[O:17])[C:15]([CH3:18])=[C:14]2[C:6]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:7][C:8]3[C:13]2=[CH:12][CH:11]=[C:10]([O:19][CH2:20][O:21][CH3:22])[CH:9]=3)[CH2:5]1)C=C.[O:27]1[CH2:32][CH2:31][O:30]CC1>O>[CH2:23]([C:6]12[CH2:5][CH:4]([CH2:1][C:31](=[O:30])[CH2:32][OH:27])[C:16](=[O:17])[C:15]([CH3:18])=[C:14]1[C:13]1[C:8](=[CH:9][C:10]([O:19][CH2:20][O:21][CH3:22])=[CH:11][CH:12]=1)[CH2:7]2)[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 67401390(2SR,9aSR)-2-allyl-9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 67398080(2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (2SR,9aSR)-2-allyl-9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (170 mg, 0.48 mmol) in dioxane (9 mL) was diluted with water (3 mL) and treated with a single crystal of OSO4 followed by NaIO4 (125 mg, 0.58 mmol). The mixture was stirred at room temperature for 15 minutes, treated with more NaIO4 (132 mg, 0.62 mmol), and stirred an additional 30 minutes at room temperature. Workup provided a gum which was purified by PLC on two 0.1×20×20 cm silica gel GF plates, developing twice with 4:1 hexanes-EtOAc. The minor UV visible band provided (2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (26 mg) as an oil. The major UV visible band afforded (2RS,9aSR)-9a-butyl-7-methoxymethoxy-4-methyl-2-(2-oxoethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (85 mg) as an oil.

Workup

  1. additiontreated with a single crystal of OSO4
  2. stirringstirred an additional 30 minutes at room temperature
  3. customWorkup provided a gum which
  4. customwas purified by PLC on two 0.1×20×20 cm silica gel GF plates

Sources & evidence

ORD record
ord-30c070b61f1b4129a0cb3214237639c6
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Reaction notes

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