Triethylamine → HCID 118349854, 화합물

HRID 2202756노트

반응식

HRID 2202756 반응식
C(N(CC)CC)C.[CH3:8][C:9]1([CH3:16])[CH2:13][NH:12][C@@H:11]([CH2:14][OH:15])[CH2:10]1.[S:17](Cl)(Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:8][C:9]1([CH3:16])[CH2:13][N:12]2[S:17](=[O:19])(=[O:18])[O:15][CH2:14][C@H:11]2[CH2:10]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 98601535HCID 98601535, 화합물

생성물 1

HCID 118349854HCID 118349854, 화합물수율 21%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of triethylamine (4.94 mL, 35.4 mmol) and (R)-(4,4-dimethylpyrrolidin-2-yl)methanol (2.29 g, 17.72 mmol) in DCM (89 mL) was cooled to −78° C. To this mixture was added sulfuryl chloride (1.0 M in DCM, 21.27 mL, 21.27 mmol) over 15 seconds. The reaction was maintained at this temperature for ˜3 h, allowed to warm to room temperature and stirred overnight (16 h). The mixture washed with aqueous 1 N HCl (30 mL×2), brine (40 mL), dried over MgSO4, filtered and concentrated affording crude product as a brown-orange oil that crystallized upon standing. The crude material was absorbed onto a plug of silica gel and purified by chromatography on an ISCO Combiflash™ RF (40 g Grace Reverlis column, using a gradient of 0-60% EtOAc in heptane) affording (R)-5,5-dimethyltetrahydro-3H-pyrrolo[1,2-c][1,2,3]oxathiazole 1,1-dioxide (708 mg, 3.70 mmol, 21% yield) as a white crystalline solid. MS (ESI) 192.1 [M+H]+.

후처리

  1. temperatureThe reaction was maintained at this temperature for ˜3 h
  2. washThe mixture washed with aqueous 1 N HCl (30 mL×2), brine (40 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customaffording crude product as a brown-orange oil
  7. customthat crystallized
  8. customThe crude material was absorbed onto a plug of silica gel
  9. custompurified by chromatography on an ISCO Combiflash™ RF (40 g Grace Reverlis column

출처 및 근거

ORD 기록
ord-928d7c6de51045809e1d882f6d679a52
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365522B2

반응 노트

불러오는 중…