Chlorotrimethylsilane → tert-butyl (2R,3S)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 604856ノート

反応式

HRID 604856 の反応式
[Li+].[BH4-].C[Si](Cl)(C)C.[C:8]([O:12][C:13]([N:15]1[CH2:19][CH2:18][C@H:17]([OH:20])[C@H:16]1[C:21](O)=[O:22])=[O:14])([CH3:11])([CH3:10])[CH3:9]>C1COCC1>[OH:20][C@H:17]1[CH2:18][CH2:19][N:15]([C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])[C@@H:16]1[CH2:21][OH:22]

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 14037017(2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

生成物 1

HCID 10910976tert-butyl (2R,3S)-3-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a 0° C. suspension of LiBH4 (2.0 equiv) in THF (0.5 M) was slowly added TMSCl (4.0 equiv) by syringe. After stirring at room temperature for 30 minutes, (2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid (1.0 equiv) was then added, and the resulting mixture was stirred at room temperature overnight. The reaction was quenched by the careful addition of sat'd. aq. NaHCO3, and the mixture was diluted with EtOAc, and the organic layer was washed twice with sat'd. aq. NaHCO3, once with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The title compound was isolated in 55% yield and used without further purification.

後処理

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe reaction was quenched by the careful addition of sat'd
  3. additionaq. NaHCO3, and the mixture was diluted with EtOAc
  4. washthe organic layer was washed twice with sat'd
  5. dry with materialaq. NaHCO3, once with brine, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-492f5244f08a436a89656473b5033dae
出典データセット
uspto-grants-2011_03
特許番号
US07910743B2

反応ノート

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