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Aniline → (2-Oxo-1-(3-phenylamino-benzyl)-azepan-3-yl]-carbamic acid tert-butyl ester

HRID 1392063
ノート
印刷プレビュー

反応式

HRID 1392063 の反応式
[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18](I)[CH:17]=2)[C:9]1=[O:23])([CH3:4])([CH3:3])[CH3:2].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CC(C)([O-])C.[Na+]>C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.O.CC(O)=O.CC(O)=O.[Pd]>[C:1]([O:5][C:6](=[O:24])[NH:7][CH:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:17]=2)[C:9]1=[O:23])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 6115AnilineHCID 23555228[1-(3-Iodo-benzyl)-2-oxo-azepan-3-yl]-carbamic acid tert-butyl esterHCID 23676156Sodium t-butoxide

生成物 1

HCID 68950358(2-Oxo-1-(3-phenylamino-benzyl)-azepan-3-yl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 4

HCID 4144353Palladium (II) acetate触媒
HCID 962
Water
溶媒
HCID 1140Toluene溶媒2 回
HCID 634876Binap, (A+-)-溶媒2 回

実験手順

In a 100 ml round bottomed flask Binap, (S)-(−)2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl, (0.210 g, 0.3375 mmol) dissolved in 15 mL toluene was stirred at 80° for 1 minute. To the flask cooled to room temperature under inert atmosphere Pd(OAC)2 (0.050 g, 0.225 mmol) was added and the solution was stirred at room temperature for 2 minutes. To the reaction mixture [1-(3-Iodo-benzyl)-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (1.0 g, 2.25 mmol) dissolved in 15 mL toluene, aniline (1.047 g, 11.25 mmol) and Sodium tert-butoxide (0.259 g, 2.70 mmol) were added and the solution was stirred at 80° C. for 18 h. The reaction was cooled to room temperature, diluted with 200 mL of water, and extracted twice with 100 mL of ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated to an oil. The oil was purified on flash silica gel column using 10-30% ethyl acetate in hexanes as eluent to yield 0.562 g (61%). MS (ESI) M+H=432.5

後処理

  1. additionwas added
  2. stirringthe solution was stirred at room temperature for 2 minutes
  3. stirringthe solution was stirred at 80° C. for 18 h
  4. extractionextracted twice with 100 mL of ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customThe oil was purified on flash silica gel column
  9. customto yield 0.562 g (61%)

出典と根拠

ORDレコード
ord-b8a6ffd2d4d44fc6a5411ec099d7b16c
出典データセット
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07342008B2

反応ノート

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