Water → HCID 67072583, 화합물

HRID 1948147노트

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HRID 1948147 반응식
[CH:1]1([CH2:4][C:5]2([CH:15]=O)[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[CH3:17][C:18]([S:21]([NH2:23])=[O:22])([CH3:20])[CH3:19].O>O1CCCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH:1]1([CH2:4][C:5]2([CH:15]=[N:23][S:21]([C:18]([CH3:20])([CH3:19])[CH3:17])=[O:22])[CH2:6][CH2:7][C:8]3([O:9][CH2:10][CH2:11][O:12]3)[CH2:13][CH2:14]2)[CH2:2][CH2:3]1

참가 물질

6

반응물 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 866563378-Cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde

생성물 1

HCID 67072583HCID 67072583, 화합물

시약·촉매·용매 2

HCID 76524Titanium tetraethoxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

The crude aldehyde was dissolved in tetrahydrofuran (40 mL) and 2-methyl-2-propanesulfinamide (1.81 g, 14.9 mmol, 1.1 eq.) and titanium(IV) ethoxide (4.27 mL, 20.3 mmol, 1.5 eq.) were added. The resulting mixture was stirred for 5 h under reflux and 16 h at room temperature, before being treated with water (10 mL) and filtered through celite. The filter cake was washed with ethyl acetate, the aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulphate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane) to yield 1.90 g of the title compound (19). Rt=1.58 min (Method B). Detected mass: 328.3 (M+H+).

후처리

  1. filtrationfiltered through celite
  2. washThe filter cake was washed with ethyl acetate
  3. customthe aqueous layer was separated
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-909d78b107ad44cbb988c506077796e1
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399482B2

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