Lauric Acid → 1-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine

HRID 2395713노트

반응식

HRID 2395713 반응식
[C:1]([OH:14])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(Cl)(=O)C(Cl)=O.[Si:21]([O:28][CH:29]1[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[O:14]=[C:1]([N:31]1[CH2:32][CH2:33][CH2:34][CH:29]([O:28][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])[CH2:30]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

참가 물질

7

반응물 4

HCID 3893Lauric AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 223524143-((Tert-butyldimethylsilyl)oxy)piperidine

생성물 1

HCID 189895461-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매3회

반응 조건

온도
0 °C

실험 절차

Dissolve lauric acid (0.77 g) in methylene chloride (50mL) and cool to 0° C. Add oxalyl chloride (0.37 mL) and dimethylformamide (3 drops). Allow to warm to room temperature and stir for 1 hour. Add, by dropwise addition, to a solution of 3-(O-tert-butyldimethylsilyloxy)piperidine (0.76 g, 3.5 mmol) and triethylamine (1 mL) in methylene chloride (20 mL). Stir overnight. Dilute with methylene chloride (50 mL) and separate the organic phase. Wash twice with 10% sodium hydroxide, once with 10% hydrochloric acid, and once with saturated sodium hydrogen carbonate and once with brine. Dry (Na2SO4) and evaporate the solvent in vacuo to give 1-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine.

후처리

  1. temperatureAllow to warm to room temperature
  2. stirringStir overnight
  3. customseparate the organic phase
  4. washWash twice with 10% sodium hydroxide, once with 10% hydrochloric acid
  5. dry with materialDry (Na2SO4)
  6. customevaporate the solvent in vacuo

출처 및 근거

ORD 기록
ord-09da1355281f47208f3af32d81f56483
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05489600

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