Sodium Carbonate → (4R,9aR)-4,6,7-Trimethyl-3,4,9,9a-tetrahydro-1 H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 1272127

반응식

HRID 1272127 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH3:22])=[C:14](Br)[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24](=O)([O-])[O-].[Na+].[Na+].CB1OB(C)OB(C)O1.[OH-].[Na+]>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH3:22])=[C:14]([CH3:24])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 574072TrimethylboroxineHCID 69357585(4R,9aR)-7-Bromo-4,6-dimethyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

생성물 1

HCID 69357909(4R,9aR)-4,6,7-Trimethyl-3,4,9,9a-tetrahydro-1 H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester수율 66%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
100 °C

실험 절차

To a solution of 0.30 g (0.78 mmol) (4R,9aR)-7-bromo-4,6-dimethyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (example 6, intermediate) in 15 mL dimethoxyethane was added 9 mg tetrakis(triphenylphosphine)palladium. After 20 min. 0.25 g (2.35 mmol) sodium carbonate in 8 mL water and 132 μl (0.94 mmol) trimethylboroxine were added and the reaction was stirred at 100° C. for 3 h. The reaction was cooled to room temperature then poured into 1M aqueous sodium hydroxide solution and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica gel with ethyl acetate:n-hexane (1:2) as eluant to give the product as a light yellow oil (66.0%).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel with ethyl acetate:n-hexane (1:2) as eluant

출처 및 근거

ORD 기록
ord-a3d843c290264c8b80d9c6c2fa7ecab9
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208494B2

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