HCID 59201637, 화합물 → HCID 59201552, 화합물

HRID 451880노트

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HRID 451880 반응식
O[C:2]1([CH2:5][CH2:6][C@@H:7]([CH2:23][O:24]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:8][C@H:9]2[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:4][CH2:3]1.C[Mg+].[Br-]>C1COCC1>[CH2:4]1[C:2]2([CH2:5][CH2:6][C@H:7]([CH2:8][C@H:9]3[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]3[C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:23][O:24]2)[CH2:3]1

참가 물질

4

반응물 2

HCID 59201637HCID 59201637, 화합물HCID 178418689HCID 178418689, 화합물

생성물 1

HCID 59201552HCID 59201552, 화합물수율 91%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The (S)-tert-butyl 4-((R)-4-(1-hydroxycyclopropyl)-2-(tosyloxymethyl)butyl)-2,2-dimethyloxazolidine-3-carboxylate was dissolved in 30 mL of THF and MeMgBr (7.0 mL of a 3.0 M solution, 2.0 equiv) was added and the mixture heated to reflux for 56 hr. After cooling to ambient the mixture was quenched by addition of water and the mixture transferred to a separatory funnel. The layers were separated and the organic layer were washed with brine, dried over Na2SO4, filtered and evaporated. The pyran derivative was purified by flash chromatography on silica (40 g) eluting with 0-29% EtOAc in hexanes. This afforded 1.05 g (91% yield) of (S)-tert-butyl 4-(((R)-4-oxaspiro[2.5]oct-6-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate. MS ESI +ve m/z 348 (M+Na).

후처리

  1. temperaturethe mixture heated
  2. temperatureto reflux for 56 hr
  3. temperatureAfter cooling to ambient the mixture
  4. customwas quenched by addition of water
  5. customthe mixture transferred to a separatory funnel
  6. customThe layers were separated
  7. washthe organic layer were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe pyran derivative was purified by flash chromatography on silica (40 g)
  12. washeluting with 0-29% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-44aebcf8fbcc48bea7f5e7236bcd7c9a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

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