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 7869노트

반응식

HRID 7869 반응식
[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]

참가 물질

4

반응물 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

생성물 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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-30c070b61f1b4129a0cb3214237639c6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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