(5S)-2-(4-bromophenyl)-5-isobutyl-1,3-dioxolan-4-one → (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid

HRID 1180370ノート

反応式

HRID 1180370 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][C:11](=[O:13])[C@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[O:9]2)=[CH:4][CH:3]=1.[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC.[Cl-].[Zn+2].[Cl-]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:12])=[O:13])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 69473106(5S)-2-(4-bromophenyl)-5-isobutyl-1,3-dioxolan-4-oneHCID 178418255HCID 178418255、化合物

生成物 1

HCID 69470808(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 3283Diethyl Ether溶媒3 回

反応条件

温度
0 °C

実験手順

Zinc chloride (1.12 l of 1M solution in ether, 1120 mmol) was added to 500 ml ether at −40° C. (5S)-2-(4-bromophenyl)-5-isobutyl-1,3-dioxolan-4-one (3:2 mixture of cis/trans) (56 g, 187 mmol) was then added dropwise in 200 ml ether (over 15 min), followed by phenylmagnesium bromide (125 ml of a 3M solution in ether, 374 mmol) (dropwise over 45 min). The solution was stirred at 0° C. for 2 hours. The reaction was quenched at 0° C. with 800 ml of a saturated solution of NH4Cl, the phases were separated and the aqueous layer extracted with 800 ml ether. The organic layers were combined, washed with brine, dried with MgSO4 and the solvent was removed. (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid (de=86%) was obtained after purification on silica gel (5% ethyl acetate/toluene).

後処理

  1. customdropwise over 45 min
  2. customThe reaction was quenched at 0° C. with 800 ml of a saturated solution of NH4Cl
  3. customthe phases were separated
  4. extractionthe aqueous layer extracted with 800 ml ether
  5. washwashed with brine
  6. dry with materialdried with MgSO4
  7. customthe solvent was removed

出典と根拠

ORDレコード
ord-34803b8b41f64fb8884fe156d307df9c
出典データセット
uspto-grants-2007_10
特許番号
US07279478B2

反応ノート

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