1-Iodopropane → (2SR,9aRS)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-2-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7860

반응식

HRID 7860 반응식
[CH2:1]([C:5]12[CH2:17][CH:16]([CH3:18])[C:15](=[O:19])[C:14]([CH3:20])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:21][CH2:22][O:23][CH3:24])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].[Li+].[CH3:26][CH:27]([N-]C(C)C)C.I[CH2:34]CC>C1COCC1>[CH2:1]([C:5]12[CH2:17][C:16]([CH3:34])([CH2:18][CH2:26][CH3:27])[C:15](=[O:19])[C:14]([CH3:20])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:21][CH2:22][O:23][CH3:24])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 3

HCID 336431-IodopropaneHCID 2724682Lithium diisopropylamideHCID 67401243(2SR,9aSR)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

생성물 1

HCID 67401329(2SR,9aRS)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-2-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A solution of (2SR,9aSR)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (110 mg, 0.34 mmol) in anhydrous THF (1.5 mL) was cooled in an ice bath, stirred under a nitrogen atmosphere, and treated with 0.4M LDA in THF (1 mL, 0.4 mmol). After stirring at 0° C. for 30 minutes, the solution was cooled to −78° C. and treated with iodopropane (0.170 mL, 1.7 mmol). The resulting mixture was allowed to gradually warm to room temperature, then stirred at room temperature overnight. Workup as described in step 2 afforded a crude product (112 mg) which was purified by PLC on a 0.1×20×20 cm silica gel GF plate, using 10:1 hexanes-EtOAc as developing solvent. The band at Rf 0.20-0.27 gave recovered starting material (39 mg) and the band at Rf 0.31-0.38 afforded the product (2SR,9aRS)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-2-propyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (41 mg) as an oil.

후처리

  1. stirringAfter stirring at 0° C. for 30 minutes
  2. temperatureto gradually warm to room temperature
  3. stirringstirred at room temperature overnight
  4. customafforded a crude product (112 mg) which
  5. customwas purified by PLC on a 0.1×20×20 cm silica gel GF plate
  6. customThe band at Rf 0.20-0.27 gave
  7. customrecovered

출처 및 근거

ORD 기록
ord-62b89ac0566e47018eebadecdf9ff60c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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