ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

1-Bromo-4-(trifluoromethoxy)benzene → 1-(Tert-butoxycarbonyl)-4-[[4-(trifluoromethoxy)phenyl]amino]piperidine

HRID 511103
ノート
印刷プレビュー

反応式

HRID 511103 の反応式
CC(C)([O-])C.[Na+].Br[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([NH:32][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]
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 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 12682914-Amino-1-Boc-piperidineHCID 23676156Sodium t-butoxide

生成物 1

HCID 66237091-(Tert-butoxycarbonyl)-4-[[4-(trifluoromethoxy)phenyl]amino]piperidine収率 64.7%

試薬・触媒・溶媒 4

HCID 634876Binap, (A+-)-触媒
HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Tris(dibenzylideneacetone)dipalladium (30 mg; 0.03 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (62 mg; 0.1 mmol), sodium tert-butoxide (240 mg; 2.5 mmol), 1-bromo-4-trifluoromethoxy-benzene (410 mg; 1.7 mmol) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (421 mg; 2.1 mmol) are suspended in dry toluene (5 mL) and the mixture is irradiated in a mono-mode microwave oven for 30 minutes at 120° C. The mixture is then cooled down to room temperature, is diluted with ethyl acetate (15 mL), filtered over Celite and concentrated under reduced pressure. The crude residue is then diluted in dichloromethane (15 mL) and filtered over a short silica gel pad. The desired product is eluted from the silica gel pad (dichloromethane (150 mL) followed by dichloromethane:methanol 98:2 (100 mL)). The fractions of interest are collected, pooled and concentrated under reduced pressure to afford the desired product (396 mg; 1.1 mmol).

後処理

  1. customthe mixture is irradiated in a mono-mode microwave oven for 30 minutes at 120° C
  2. filtrationfiltered over Celite
  3. concentrationconcentrated under reduced pressure
  4. additionThe crude residue is then diluted in dichloromethane (15 mL)
  5. filtrationfiltered over a short silica gel pad
  6. washThe desired product is eluted from the silica gel pad (dichloromethane (150 mL) followed by dichloromethane:methanol 98:2 (100 mL))
  7. customThe fractions of interest are collected
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f5fb15e956b5417593a7a9f8ee985fac
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096524B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート