Aluminium lithium hydride → 3-Pyrrolidinemethanol, 4-(4-chlorophenyl)-3-methyl-1-(phenylmethyl)-

HRID 1891321ノート

反応式

HRID 1891321 の反応式
C([O:3][C:4]([C:6]1([CH3:25])[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:9][N:8]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:18]([N:8]1[CH2:9][CH:10]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[C:6]([CH2:4][OH:3])([CH3:25])[CH2:7]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 66653488HCID 66653488、化合物

生成物 1

HCID 666532933-Pyrrolidinemethanol, 4-(4-chlorophenyl)-3-methyl-1-(phenylmethyl)-収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of (3RS,4RS)-1-benzyl-4-(4-chloro-phenyl)-3-methyl-pyrrolidine-3-carboxylic acid ethyl ester (5.75 g, 16.7 mmol) in THF (200 mL) at 0° C., was added portion wise LiAlH4 (381 mg, 10.0 mmol) over 20 minutes. After one hour at this temperature, the reaction mixture was carefully quenched by addition of icy water and then of an aqueous solution of NaHCO3. The product was extracted with EtOAc several times, the combined organic phases were dried over NA2SO4 and purification by column chromatography (SiO2, EtOAc/H 1:4 to 1:1) yielded the title product (4.0 g, 76%) as a colorless viscous oil. ES-MS m/e: 316.2 (M+H+).

後処理

  1. customthe reaction mixture was carefully quenched by addition of icy water
  2. extractionThe product was extracted with EtOAc several times
  3. dry with materialthe combined organic phases were dried over NA2SO4 and purification by column chromatography (SiO2, EtOAc/H 1:4 to 1:1)

出典と根拠

ORDレコード
ord-33bc395525f94673a4c5ad776ea16a7b
出典データセット
uspto-grants-2013_08
特許番号
US08507535B2

反応ノート

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