1,2-Dichloroethane → Bis(3-fluorophenyl)methyl 1-methylpiperidine-4-carboxylate

HRID 1910515ノート

反応式

HRID 1910515 の反応式
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[F:26][C:27]1[CH:28]=[C:29]([CH:33]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=2)O)[CH:30]=[CH:31][CH:32]=1.C(N(CC)CC)C>C1COCC1>[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH:33]([C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([F:26])[CH:28]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=2)=[O:10])[CH2:5][CH2:4]1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2758250Bis(3-fluorophenyl)methanolHCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)

生成物 1

HCID 70925814Bis(3-fluorophenyl)methyl 1-methylpiperidine-4-carboxylate収率 31.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

1-Methylpiperidine-4-carboxylic acid hydrochloride (250 mg, 1.39 mmol), EDC (400 mg, 2.09 mmol), and HOBT (320 mg, 2.09 mmol) were dissolved in dry THF (10 ml). Bis(3-fluorophenyl)methanol (337 mg, 1.53 mmol) was dissolved in dry THF (4 ml) and then added to the reaction mixture. Triethylamine (6790, 4.87 mmol) was finally added, and the resulting reaction was stirred at room temperature overnight. The reaction was evaporated, and the residue was taken up with EtOAc and washed with water and sat.NaHCO3. The organic phase was dried over sodium sulfate, filtered, and evaporated under vacuum. The crude was purified by flash chromatography (DCM/MeOH=9/1) to afford bis(3-fluorophenyl)methyl 1-methylpiperidine-4-carboxylate (150 mg).

後処理

  1. additionadded to the reaction mixture
  2. customthe resulting reaction
  3. customThe reaction was evaporated
  4. washwashed with water
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe crude was purified by flash chromatography (DCM/MeOH=9/1)

出典と根拠

ORDレコード
ord-e4fcb5cc8dd94d87a273c972c84bc850
出典データセット
uspto-grants-2013_12
特許番号
US08604015B2

反応ノート

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