Hydrochloric Acid → 2-Propanyl 4-[(3S,5aR,6R,7R,8aS)-7-(tetrahydro-2H-pyran-2-yloxy)-6-vinyloctahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

HRID 573534ノート

反応式

HRID 573534 の反応式
[CH3:1][Si](C)(C)N[Si](C)(C)C.[Na].[CH:11]([C@@H:13]1[C@@H:22]2[C@@H:16]([O:17][CH2:18][C@@H:19]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:20][CH2:21]2)[CH2:15][C@H:14]1[O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)=O.Cl>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[O:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH:33]1[O:32][C@@H:14]1[CH2:15][C@@H:16]2[O:17][CH2:18][C@@H:19]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:20][CH2:21][C@@H:22]2[C@H:13]1[CH:11]=[CH2:1]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 45051731Sodium hexamethyidisilazaneHCID 866653202-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-formyl-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

生成物 1

HCID 867043622-Propanyl 4-[(3S,5aR,6R,7R,8aS)-7-(tetrahydro-2H-pyran-2-yloxy)-6-vinyloctahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Methyltriphenylphosphonium bromide (2.60 g) was suspended in THF (10 mL), and followed by cooling to 0° C. Sodium hexamethyldisilazane (7.0 mL, 1 mol/L THF solution) was added, followed by stirring at the same temperature for 30 minutes. A THF (1 mL) solution of the compound (1.0 g) produced in Example 13 was added dropwise, followed by stirring at the same temperature for 1 hour. An extract obtained by pouring the reaction solution to 1 N hydrochloric acid cooled to 0° C. and extracting with ethyl acetate was washed with water, an aqueous saturated sodium bicarbonate solution and a saturated saline; dried with anhydrous magnesium sulfate; and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain a titled compound (967 mg) having the following physical property values.

後処理

  1. stirringby stirring at the same temperature for 1 hour
  2. customAn extract obtained
  3. temperaturecooled to 0° C.
  4. extractionextracting with ethyl acetate
  5. washwas washed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationand then concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-bd540076a60543fd9d194c3f5b1d297e
出典データセット
uspto-grants-2015_05
特許番号
US09029574B2

反応ノート

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