Ammonium Chloride → 1-[2-(2-Hydroxymethyl-4-bromophenoxy)ethyl]pyrrolidine

HRID 734846ノート

反応式

HRID 734846 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:16][CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:12]([CH:15]=1)[CH:13]=[O:14].[Cl-].[NH4+]>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:16][CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:12]([CH2:13][OH:14])[CH:15]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 176209185-Bromo-2-(2-pyrrolidin-1-ylethoxy)benzaldehydeHCID 21226445Aluminium lithium hydride2 回

生成物 1

HCID 211828631-[2-(2-Hydroxymethyl-4-bromophenoxy)ethyl]pyrrolidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3.4 mL (3.40 mmol) of a lithium aluminum hydride solution (1M in THF) was added under argon at 0° C. to a solution of 1.00 g (3.35 mmol) of 5-bromo-2-(2-pyrrolidin-1-ylethoxy)benzaldehyde (Example 24.1a) in 20 mL of THF and the mixture was stirred for 2 hours at RT. A further 6.8 mL of lithium aluminum hydride solution (1M in THF) was added and the mixture was stirred for 2 hours at RT. The reaction mixture was slowly combined with sat. aqueous ammonium chloride solution and the aqueous phase was exhaustively extracted with EtOAc. The combined organic extracts were dried over magnesium sulfate and evaporated down in vacuo. As some starting material could still be detected, the reaction was repeated with 1.7 mL of lithium aluminum hydride solution (1M in THF) and the working up was repeated. Yield: 0.82 g (81% of theoretical); C13H18BrNO2 (M=300.192); calc.: molpeak (M+H)+: 300/302 (Br); found: molpeak (M+H)+: 300/302 (Br); HPLC-MS: 4.62 minutes (method A).

後処理

  1. stirringthe mixture was stirred for 2 hours at RT
  2. extractionthe aqueous phase was exhaustively extracted with EtOAc
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. customevaporated down in vacuo
  5. custom4.62 minutes (method A)

出典と根拠

ORDレコード
ord-92704a9ac97644fcae8dba60b1d78275
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

反応ノート

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