Hydrochloric Acid → Benzyl 1-(1-tert-butoxycarbonyl-3-hydroxy-1-propylamino)cyclohexanecarboxylate

HRID 1459892ノート

反応式

HRID 1459892 の反応式
[C:1]([O:5][C:6]([CH:8]([NH:12][C:13]1([C:19]([OH:21])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:9][CH:10]=C)=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+].[BH4-].[Na+].Cl.[OH2:31]>O1CCOCC1.C(O)(C)(C)C.CO.[Os](=O)(=O)(=O)=O>[CH2:19]([O:21][C:19]([C:13]1([NH:12][CH:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][OH:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 23667635Sodium periodateHCID 54371918(1-Tert-butoxycarbonylbut-3-enylamino)-cyclohexanecarboxylic acid

生成物 1

HCID 53835842Benzyl 1-(1-tert-butoxycarbonyl-3-hydroxy-1-propylamino)cyclohexanecarboxylate

試薬・触媒・溶媒 4

HCID 30318Osmium Tetroxide触媒HCID 887Methanol溶媒HCID 6386tert-Butanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of (1-tert-butoxycarbonylbut-3-enylamino)-cyclohexanecarboxylic acid (0.5 g, 1.29 mmol) in dioxane (5 mL) and water (5 mL) was added a 2.5 weight % solution of osmium tetroxide in tert-butanol (0.05 mL). After 20 minutes, sodium periodate (0.88 g, 4.13 mmol) was added in small portions over another period of 20 minutes. The mixture was stirred at room temperature for 6 hours and was quenched by addition of a saturated aqueous solution of sodium bicarbonate. The mixture was extracted with ethyl acetate and the extract was washed with brine, dried over magnesium sulfate, and concentrated under vacuum to give an oil. The oil was dissolved in methanol (12 mL) and sodium borohydride (137 mg, 3.61 mmol) was added. The mixture was stirred overnight. A 1M aqueous solution of hydrochloric acid was added and, after stirring for 10 minutes, the solvent was removed under vacuum. The residue was partitioned between a saturated aqueous solution of sodium bicarbonate and ethyl acetate. The organic layer was washed with brine dried over magnesium sulfate, and concentrated under vacuum to give an oil. The oil was chromatographed on silica gel eluting with 10% ethyl acetate in methylene chloride to provide 1-(1-tert-butoxycarbonyl-3-hydroxy-propylamino)cyclohexanecarboxylic acid benzyl ester as an oil, 469 mg (66%).

後処理

  1. customwas quenched by addition of a saturated aqueous solution of sodium bicarbonate
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give an oil
  7. stirringThe mixture was stirred overnight
  8. stirringafter stirring for 10 minutes
  9. customthe solvent was removed under vacuum
  10. customThe residue was partitioned between a saturated aqueous solution of sodium bicarbonate and ethyl acetate
  11. washThe organic layer was washed with brine
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated under vacuum
  14. customto give an oil
  15. customThe oil was chromatographed on silica gel eluting with 10% ethyl acetate in methylene chloride

出典と根拠

ORDレコード
ord-79c338ecbe8a48c686f556dd83e92102
出典データセット
uspto-grants-1998_12
特許番号
US05854275

反応ノート

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