Potassium bisulfate → Tert-butyl N-(1-oxohex-4-YN-2-YL)carbamate

HRID 1956685노트

반응식

HRID 1956685 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([NH:14][CH:15]([CH2:22][C:23]#[C:24][CH3:25])[C:16](N(OC)C)=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].S([O-])(O)(=O)=O.[K+]>CCOCC.O>[C:7]([O:11][C:12]([NH:14][CH:15]([CH2:22][C:23]#[C:24][CH3:25])[CH:16]=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8]

참가 물질

6

반응물 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 21258867Carbamic acid, [1-[(methoxymethylamino)carbonyl]-3-pentynyl]-, 1,1-dimethylethyl ester

생성물 1

HCID 45092115Tert-butyl N-(1-oxohex-4-YN-2-YL)carbamate

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매2회

실험 절차

A suspension of lithium aluminum hydride (1.56 g, 41.1 mmol) in ether (150 mL) was stirred at room temperature for 30 minutes. The solution was cooled to -55° C. under nitrogen, and a solution of the product from Step J (11.10 g, 41.1 mmol) in ether (150 mL) was added over 15 min, maintaining the temperature below -50° C. When the addition was complete, the reaction was warmed to 5° C., then recooled to -40° C. A solution of potassium hydrogen sulfate (21.8 g) in 25 mL water was slowly added, maintaining the temperature below -35° C. The mixture was warmed to room temperature and stirred for one hour, filtered through Celite, and concentrated in vacuo to provide the title aldehyde.

후처리

  1. temperatureThe solution was cooled to -55° C. under nitrogen
  2. temperaturemaintaining the temperature below -50° C
  3. additionWhen the addition
  4. temperaturethe reaction was warmed to 5° C.
  5. customrecooled to -40° C
  6. temperaturemaintaining the temperature below -35° C
  7. temperatureThe mixture was warmed to room temperature
  8. stirringstirred for one hour
  9. filtrationfiltered through Celite
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-41bcdf6c8f63496e8b439867b782e0bb
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05780492

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