Lithium aluminum hydride → (2S,4R)-4-Phenyl-2-pyrrolidinemethanol

HRID 557923ノート

反応式

HRID 557923 の反応式
[AlH4-].[Li+].[C:3]1([C@@H:9]2[CH2:13][NH:12][C@H:11]([C:14](OC)=[O:15])[CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCCC1>[C:3]1([C@@H:9]2[CH2:13][NH:12][C@H:11]([CH2:14][OH:15])[CH2:10]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 28112Lithium aluminum hydrideHCID 14102971HCID 14102971、化合物

生成物 1

HCID 57368261(2S,4R)-4-Phenyl-2-pyrrolidinemethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Lithium tetrahydroaluminate in tetrahydrofuran (1.00 M, 1.00 mL) was added to methyl (2S,4R)-4-phenylpyrrolidine-2-carboxylate (103.0 mg, 0.0005018 mol) in tetrahydrofuran (3.00 mL, 0.0370 mol) at 0° C. Then the ice-water bath was removed and the reaction mixture was stirred at rt for 1 h and was quenched with brine (1 mL). The resulting mixture was extracted with ethyl acetate (2×2 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product which was directly used in the next step without further purification.

後処理

  1. customThen the ice-water bath was removed
  2. customwas quenched with brine (1 mL)
  3. extractionThe resulting mixture was extracted with ethyl acetate (2×2 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-1886924778be478cb073348f034705f8
出典データセット
uspto-grants-2011_11
特許番号
US08058288B2

反応ノート

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