Aluminium lithium hydride → (4R)-4-Hydroxy-1-methyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine

HRID 743300ノート

反応式

HRID 743300 の反応式
C(O[C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][CH:9]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:13][C@H:11]1[CH2:12][N:8]([CH3:6])[CH:9]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:10]1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 54118331(4R)-1-t-butoxycarbonyl-4-hydroxy-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine

生成物 1

HCID 54021671(4R)-4-Hydroxy-1-methyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine収率 63.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Following a procedure similar to that described in Example 38, 300 mg of (4R)-1-t-butoxycarbonyl-4-hydroxy-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine [prepared as described in Example 65(b)] were reacted with 85.9 mg of lithium aluminum hydride dispersed in 30 ml of tetrahydrofuran. The mixture was then worked up as described in Example 38, and the crude product thus obtained was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 150 mg (yield 63%) of the title compound as a colorless oil.

後処理

  1. customthe crude product thus obtained
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of methylene chloride and methanol as the eluent

出典と根拠

ORDレコード
ord-82557143a4c44b10af182ae7deaecac3
出典データセット
uspto-grants-1996_09
特許番号
US05556864

反応ノート

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