Imidazole → (2S,4R)-1-tert-Butyl 2-methyl 4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate

HRID 81125

반응식

HRID 81125 반응식
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C)C=O>[Si:23]([O:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

참가 물질

5

반응물 3

HCID 795Imidazole2회HCID 28928tert-Butyldimethylsilyl chlorideHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

생성물 1

HCID 10618477(2S,4R)-1-tert-Butyl 2-methyl 4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-tert-butyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate (970 g) in N,N-dimethylformamide (1000 mL) was added imidazole (591 g) at 0° C. Upon dissolution of the imidazole, tert-butyldimethylsilyl chloride (652 g) was added at 0° C. The reaction was stirred for 16 hours at room temperature, cooled to 0° C., and quenched with water (2.25 L). The mixture was extracted with ethyl acetate (4×), and the combined organic layer was washed with brine (3×), dried over magnesium sulfate, filtered, and concentrated to give 1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate. The residue was used directly without further purification.

후처리

  1. additionwas added at 0° C
  2. temperaturecooled to 0° C.
  3. customquenched with water (2.25 L)
  4. extractionThe mixture was extracted with ethyl acetate (4×)
  5. washthe combined organic layer was washed with brine (3×)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d5f0391c05a1424aa45aba621192dc61
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846657B2

연결된 노트

불러오는 중…