P-Toluenesulfonamide → 6-Tosyl-2-oxa-6-azaspiro[3.3]heptane

HRID 1410088노트

반응식

HRID 1410088 반응식
[OH-].[K+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.Br[CH2:15][C:16]([CH2:21]Br)([CH2:19]Br)[CH2:17][OH:18]>C(O)C>[C:4]1([CH3:3])[CH:5]=[CH:6][C:7]([S:10]([N:13]2[CH2:21][C:16]3([CH2:19][O:18][CH2:17]3)[CH2:15]2)(=[O:12])=[O:11])=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 6269P-ToluenesulfonamideHCID 14797Potassium HydroxideHCID 15206Pentaerythritol tribromide

생성물 1

HCID 233198916-Tosyl-2-oxa-6-azaspiro[3.3]heptane수율 69.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of KOH (4.98 g, 0.089 mol) and 4-methylbenzenesulfonamide (5.7 g, 0.033 mol) in 90 ml of ethanol, 3-bromo-2,2-bis(bromomethyl)propan-1-ol (9 g, 0.0277 mol) was added at room temperature and the reaction mixture was heated to reflux for 45 h. The solvent was removed by evaporation, 75 ml of 1 M KOH were added and the white suspension was left to stir for another 2 h at room temperature. The mixture was filtered and the white filter cake was rinsed with water until the washing water was neutral. The filter cake was dried under high vacuum to give 4.87 g 6-toluene-4-sulfonyl-2-oxa-6-azaspiro[3.3]heptane (69%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.70-7.68 (m, 2H), 7.36-7.34 (m, 2H), 4.58 (s, 4H), 3.90 (s, 4H), 2.45 (s, 3H).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 45 h
  3. customThe solvent was removed by evaporation, 75 ml of 1 M KOH
  4. additionwere added
  5. waitthe white suspension was left
  6. filtrationThe mixture was filtered
  7. washthe white filter cake was rinsed with water until the washing water
  8. customThe filter cake was dried under high vacuum

출처 및 근거

ORD 기록
ord-18ab945b6bf84d1985df8941b90708f1
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921383B2

반응 노트

불러오는 중…