Lithium Chloride → 1-(4-Fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one

HRID 271236ノート

反応式

HRID 271236 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH2:11][CH:10]([C:14](OCC)=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[Cl-].[Li+].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH:10]([CH2:14][OH:15])[CH2:11][C:12]2=[O:13])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 21935588Ethyl 1-(4-fluorophenyl)-5-oxopyrrolidine-3-carboxylate

生成物 1

HCID 104656771-(4-Fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of ethyl 1-(4-fluorophenyl)-5-oxopyrrolidine-3-carboxylate (0.25 g, 1.0 mmol) in ethanol (10 ml) was added lithium chloride (0.085 g, 2.0 mmol) and sodium borohydride (0.080 g, 2.0 mmol). The reaction was stirred 24 hours at room temperature. The solvent was removed and 30 ml water was added to the residue. The aqueous solution was acidified with conc. HCl until the pH was ˜2-3. The acidic solution was extracted was acidified with conc. HCl until the pH was ˜2-3. The acidic solution was extracted sodium sulfate and evaporated. The residue was purified using preparative TLC (15:1 DCM:MeOH) to yield 1-(4-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one (H HNMR). This was repeated twice.

後処理

  1. customThe solvent was removed
  2. addition30 ml water was added to the residue
  3. extractionThe acidic solution was extracted
  4. extractionThe acidic solution was extracted sodium sulfate
  5. customevaporated
  6. customThe residue was purified

出典と根拠

ORDレコード
ord-f843d0b7faff490c955338a32f24fd07
出典データセット
uspto-grants-2008_11
特許番号
US07452889B2

反応ノート

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