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(S)-2-(2-Bromo-6-methyl-4-nitrophenyl)-2-tert-butoxyethyl pivalate → (S)-2-(4-amino-2-bromo-6-methylphenyl)-2-tert-butoxyethyl pivalate

HRID 879272
ノート
印刷プレビュー

反応式

HRID 879272 の反応式
[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([N+:22]([O-])=O)=[CH:17][C:16]=1[Br:25])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>CCO.CCOC(C)=O.[Pt]>[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([NH2:22])=[CH:17][C:16]=1[Br:25])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])(=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

HCID 70981268(S)-2-(2-Bromo-6-methyl-4-nitrophenyl)-2-tert-butoxyethyl pivalate

生成物 1

HCID 86699788(S)-2-(4-amino-2-bromo-6-methylphenyl)-2-tert-butoxyethyl pivalate収率 82.4%

試薬・触媒・溶媒 3

HCID 23939Platinum触媒HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (S)-2-(2-Bromo-6-methyl-4-nitrophenyl)-2-tert-butoxyethyl pivalate (9 g, 0.022 mol) in EtOH (50 mL) and EtOAc (50 mL) was added Pt/C (1.4 g), and the reaction was fitted with a balloon of H2. The reaction mixture was stirred at room temperature for 3 h. TLC showed the reaction was complete. The reaction mixture was filtered over Celite. The filtrate was concentrated in vacuo to give (S)-2-(4-amino-2-bromo-6-methylphenyl)-2-tert-butoxyethyl pivalate (7 g, 82%) as brown oil, which was immediately used for next step without further purification. 1H-NMR: 400 MHz, (CDCl3) δ: 6.70 (s, 1H), 6.40 (s, 1H), 5.38 (app. s, broad, 1H), 4.22 (app. s, broad, 1H), 4.05 (app. s, broad, 1H), 3.60 (app. s, broad, 2H), 2.47 (s, 3H), 1.17 (s, 9H), 1.13 (s, 9H).

後処理

  1. customthe reaction was fitted with a balloon of H2
  2. filtrationThe reaction mixture was filtered over Celite
  3. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-881cc51598834860a425b96f12ca4756
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987250B2

反応ノート

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