TBS-COREY LACTONE ALDEHYDE → HCID 68733852、化合物

HRID 1470680ノート

反応式

HRID 1470680 の反応式
[Br-].[CH2:2]([PH3+])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CC(C)([O-])C.[K+].[Si:16]([O:23][C@@H:24]1[CH2:32][C@@H:27]2[O:28][C:29](=[O:31])[CH2:30][C@@H:26]2[C@H:25]1[CH:33]=O)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C1COCC1>[Si:16]([O:23][C@@H:24]1[CH2:32][C@@H:27]2[O:28][C:29](=[O:31])[CH2:30][C@@H:26]2[C@H:25]1[CH:33]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])([C:19]([CH3:20])([CH3:22])[CH3:21])([CH3:17])[CH3:18]

参加物

5

反応物 3

HCID 10989745TBS-COREY LACTONE ALDEHYDEHCID 23665647Potassium tert-butoxideHCID 86630288HCID 86630288、化合物

生成物 1

HCID 68733852HCID 68733852、化合物収率 91.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

n-heptylphosphonium bromide (3.185 g, 7.22 mmol) was dried under vacuum for 3 days and was then taken into dry THF (22 mL). Potassium tert-butoxide (7.2 mL, 7.2 mmol, 1 M/THF) was added and the resulting red-orange solution was stirred for 45 min. at room temperature. A solution of (3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde (5-1, 502 mg, 1.78 mmol, Cayman) in 7 mL THF was added by cannula, rinsing with 3 mL THF. After 1.5 h, the reaction was quenched by addition of saturated NH4Cl solution. The resulting mixture was extracted with ethyl acetate (3×) and the combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit) gave the title compound (595 mg, 91%).

後処理

  1. washrinsing with 3 mL THF
  2. waitAfter 1.5 h
  3. customthe reaction was quenched by addition of saturated NH4Cl solution
  4. extractionThe resulting mixture was extracted with ethyl acetate (3×)
  5. dry with materialthe combined ethyl acetate solution was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the residue by flash chromatography on silica gel (Isco Combiflash unit)

出典と根拠

ORDレコード
ord-2c611dcaa9524007ad009d5888c9284f
出典データセット
uspto-grants-2015_04
特許番号
US09006464B2

反応ノート

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