Imidazole → tert-Butyl 6-(tert-butyldimethylsilyloxy)hexylcarbamate

HRID 1019841노트

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HRID 1019841 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1.[C:21]([Si:25]([CH3:28])([CH3:27])Cl)([CH3:24])([CH3:23])[CH3:22]>C(Cl)Cl>[Si:25]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:28])[CH3:27]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 4146612tert-Butyl N-(6-hydroxyhexyl)carbamate

생성물 1

HCID 86676514tert-Butyl 6-(tert-butyldimethylsilyloxy)hexylcarbamate수율 87%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of tert-butyl 6-hydroxyhexylcarbamate (21 mmol) in CH2Cl2 (30 ml) was added imidazole (27 mmol) at 0° C. The reaction mixture was kept at 25° C. and stirred for 20 min, then cooled to 0° C. To the resulting reaction mixture was added tert-butyldimethylchlorosilane (23 mmol) dropwise over 30 min at 0° C. The reaction mixture was allowed to warm to 25° C. and stirred for 16 h and then filtered. The filtrate was washed with 1 N HCl (2×25 ml) and brine (30 ml), dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by SiO2 flash column (eluent: petroleum ether and then CH2Cl2). Yield 6.53 g (87% yield).

후처리

  1. customwas kept at 25° C.
  2. customTo the resulting reaction mixture
  3. temperatureto warm to 25° C.
  4. stirringstirred for 16 h
  5. filtrationfiltered
  6. washThe filtrate was washed with 1 N HCl (2×25 ml) and brine (30 ml)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by SiO2 flash column (eluent

출처 및 근거

ORD 기록
ord-b9f519400d5e4537b17781dabf7aa039
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716293B2

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