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Triethylamine → (4R,9aR)-6-Cyclopropylmethoxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2,7-dicarboxylic acid 2-tert-butyl ester 7-methyl ester

HRID 1272149
ノート
印刷プレビュー

反応式

HRID 1272149 の反応式
[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]([CH2:22][O:23][CH2:24][CH:25]2[CH2:27][CH2:26]2)=[C:14](Br)[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:5][C:6]([C:14]1[CH:13]=[C:12]2[C:17]([N:18]3[C@H:10]([CH2:11]2)[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:20][C@H:19]3[CH3:21])=[N:16][C:15]=1[CH2:22][O:23][CH2:24][CH:25]1[CH2:27][CH2:26]1)=[O:7]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 69357623(4R,9aR)-7-bromo-6-cyclopropylmethoxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

生成物 1

HCID 69361749(4R,9aR)-6-Cyclopropylmethoxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2,7-dicarboxylic acid 2-tert-butyl ester 7-methyl ester収率 87%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1.5 g (3.31 mmol) (4R,9aR)-7-bromo-6-cyclopropylmethoxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, 0.11 g (0.50 mmol) palladium(II) acetate, 0.68 g (1.66 mmol) 1,3-bis(diphenylphosphino)propane and 1.4 mL (1.0 g, 10.0 mmol) triethylamine in 15 mL MeOH was stirred for 48 h at 100° C. under a carbon monoxide atmosphere (50 bar). The reaction mixture was cooled to room temperature, filtered and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulphate, filtered and evaporated. The residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:3) as eluant to give the compound as a yellow oil (87%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. custompartitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:3) as eluant

出典と根拠

ORDレコード
ord-c9b65a6856b04c9ca3716675f9b24db3
出典データセット
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07208494B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート