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

HRID 604856노트

반응식

HRID 604856 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-492f5244f08a436a89656473b5033dae
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910743B2

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