Aluminium lithium hydride → (2S,4S)-2-Hydroxymethyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 238987ノート

反応式

HRID 238987 の反応式
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][N:6]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.O>O1CCCC1>[C:19]([O:18][C:16]([N:6]1[CH2:7][C@H:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:9][C@H:5]1[CH2:3][OH:2])=[O:17])([CH3:22])([CH3:21])[CH3:20]

参加物

5

反応物 3

HCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 580029141-(tert-Butyl) 2-methyl (2S,4S)-4-phenylpyrrolidine-1,2-dicarboxylate

生成物 1

HCID 58002916(2S,4S)-2-Hydroxymethyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

4.2 g of (2S,4S)-4-Phenyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (13.75 mmol) in 30 ml tetrahydrofuran were slowly added to a suspension of 0.27 g of lithium aluminium hydride in 50 ml tetrahydrofurane. Stirring was continued for 5 h at 0-5° C. and for 14 h at room temperature. For workup, a mixture of tetrahydrofurane/water (1:1) was slowly added to the reaction mixture at 0° C. The solvent was then evaporated under reduced pressure, water was added and the pH was adjusted to about 5 with 20% aqueous citric acid. The aqueous phase was extracted four times with ethyl acetate, the organic layers were combined, dried over magnesium sulphate, filtered, and the solvent was removed under reduced pressure to yield 3.85 of product.

後処理

  1. additionwas slowly added to the reaction mixture at 0° C
  2. customThe solvent was then evaporated under reduced pressure, water
  3. additionwas added
  4. extractionThe aqueous phase was extracted four times with ethyl acetate
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customto yield 3.85 of product

出典と根拠

ORDレコード
ord-d6f426645a6842ef9bac8bb00f3b9f0c
出典データセット
uspto-grants-2014_02
特許番号
US08642642B2

反応ノート

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