Aluminium lithium hydride → 2-(4-Fluoro-phenyl)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1644818ノート

反応式

HRID 1644818 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=O>C(OCC)C>[C:19]([O:18][C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C:11]1([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH2:9][OH:8])=[O:17])([CH3:22])([CH3:20])[CH3:21]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 667735252-(4-Fluoro-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

生成物 1

HCID 667735772-(4-Fluoro-phenyl)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester収率 86.8%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
-20 °C

実験手順

To a suspension of lithiumaluminiumhydride (1.5 g) in dry diethyl ether (25 mL) at −20° C. was added dropwise a solution of 2-(4-fluoro-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (4.25 g) in dry diethyl ether (20 mL) over 10 minutes. The reaction was stirred at −20° C. for 20 minutes and followed by TLC. After 30 minutes the reaction was quenched at −20° C. by adding saturated aqueous sodium sulfate solution dropwise until the lithium aluminium hydride reagent was fully quenched. Further solid sodium sulfate was added to the slurry and the mixture was allowed to warm to ambient temperature. The slurry was filtered and the solid was washed with further diethyl ether. The filtrate was collected and the diethyl ether was evaporated in vacuo to afford the desired 2-(4-fluoro-phenyl)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (3.37 g, MS (ES+): 296.3 (MH+)) as a colourless oil.

後処理

  1. customAfter 30 minutes the reaction was quenched at −20° C.
  2. additionby adding saturated aqueous sodium sulfate solution dropwise until the lithium aluminium hydride reagent
  3. customwas fully quenched
  4. additionFurther solid sodium sulfate was added to the slurry
  5. temperatureto warm to ambient temperature
  6. filtrationThe slurry was filtered
  7. washthe solid was washed with further diethyl ether
  8. customThe filtrate was collected
  9. customthe diethyl ether was evaporated in vacuo

出典と根拠

ORDレコード
ord-d5f324281e22475484adcd0e1ee5df21
出典データセット
uspto-grants-2012_02
特許番号
US08124636B2

反応ノート

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