Aluminium lithium hydride → (γS)-4-(Methylsulfonyl)-γ-phenylbenzenepropanol

HRID 1593015ノート

反応式

HRID 1593015 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:12][C:13](N2[C@H](C3C=CC=CC=3)[C@H](C)N(C)C2=O)=[O:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:29]1([C@@H:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[CH2:12][CH2:13][OH:14])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 69264112HCID 69264112、化合物

生成物 1

HCID 69264553(γS)-4-(Methylsulfonyl)-γ-phenylbenzenepropanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (4S,5R)-1-[(S)-3-(4-methanesulfonyl-phenyl)-3-phenyl-propionyl]-3,4-dimethyl-5-phenyl-imidazolidin-2-one (846 mg, 1.78 mmol) in THF (20 mL) at 0° C. was added lithium aluminium hydride (3.6 mL, 1M in THF, 3.6 mmol) and the resulting mixture was stirred for 15 min. The reaction was quenched by the addition of 2M aqueous sodium hydroxide. The phases were separated and the organic phase pre-absorbed onto a Bond Elut and eluted with a gradient of isohexane to ethyl acetate giving the sub-titled compound as a white solid (285 mg, 55%); NMR (CDCl3): 1.63 (br s, 1H), 2.33 (m, 2H), 3.00 (s, 3H), 3.59 (t, 2H), 4.28 (t, 1H), 7.23 (m, 5H), 7.43 (d, 2H), 7.82 (d, 2H).

後処理

  1. customThe reaction was quenched by the addition of 2M aqueous sodium hydroxide
  2. customThe phases were separated
  3. customthe organic phase pre-absorbed onto a Bond Elut
  4. washeluted with a gradient of isohexane to ethyl acetate giving the sub-titled compound as a white solid (285 mg, 55%)

出典と根拠

ORDレコード
ord-d5db36baf44d4d229ce0efdac31727f6
出典データセット
uspto-grants-2007_11
特許番号
US07294636B2

反応ノート

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