HCID 59201637、化合物 → HCID 59201552、化合物

HRID 451880ノート

反応式

HRID 451880 の反応式
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

参加物

4

反応物 2

HCID 59201637HCID 59201637、化合物HCID 178418689HCID 178418689、化合物

生成物 1

HCID 59201552HCID 59201552、化合物収率 91%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-44aebcf8fbcc48bea7f5e7236bcd7c9a
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

反応ノート

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