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Formic Acid → (1RS,2SR,6RS,7SR,8RS)-8-(3-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

HRID 407858
ノート
印刷プレビュー

反応式

HRID 407858 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.N1CCCCC1.[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[CH:24]1[C:32](=[O:33])[CH:31]2[CH:26]([CH:27]3[O:34][CH:30]2[CH:29]=[CH:28]3)[C:25]1=[O:35].C(O)=O>CN(C)C=O.ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([CH:29]2[CH2:28][CH:27]3[O:34][CH:30]2[CH:31]2[CH:26]3[C:25](=[O:35])[CH:24]([C:17]3[C:18]([CH3:23])=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=3[CH3:15])[C:32]2=[O:33])[CH:5]=[CH:6][CH:7]=1
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

8

反応物 4

HCID 284Formic AcidHCID 8082PiperidineHCID 707251-Fluoro-3-iodobenzeneHCID 67283862(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione

生成物 1

HCID 67284052(1RS,2SR,6RS,7SR,8RS)-8-(3-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

Bis(triphenylphosphine)palladium diacetate (20 mg, 0.024 mmol), 1-fluoro-3-iodo-benzene (104 mg, 0.47 mmol) and piperidine (0.16 ml, 1.6 mmol) are added to a solution of (1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione (0.20 g, 0.71 mmol) in dry N,N-dimethylformamide (2 ml). Formic acid (0.06 ml, 1.6 mmol) is added and the reaction mixture is heated at 50° C. for 2 hours. The reaction mixture is cooled to room temperature, water (1 ml) and dichloromethane (1 ml) are added, and the mixture is stirred for 1 hour. The two phases are separated, the organic phase collected and the solvent is evaporated. The residue is purified by preparative reverse-phase HPLC to give (1RS,2SR,6RS,7SR,8RS)-8-(3-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione.

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customThe two phases are separated
  3. customthe organic phase collected
  4. customthe solvent is evaporated
  5. customThe residue is purified by preparative reverse-phase HPLC

出典と根拠

ORDレコード
ord-4394443872004514b123596c6f130ee9
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08754242B2

反応ノート

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