Sodium borohydride → 1-Piperidinecarboxylicacid,4-hydroxy-2-methyl-,1,1-dimethylethylester,(2S,4R)-(9CI)

HRID 1022867ノート

反応式

HRID 1022867 の反応式
[BH4-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH:11]1[CH3:17])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]>CCO>[C:3]([N:10]1[CH2:15][CH2:14][C@@H:13]([OH:16])[CH2:12][C@@H:11]1[CH3:17])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 12992764tert-Butyl 2-methyl-4-oxopiperidine-1-carboxylate

生成物 1

HCID 450974411-Piperidinecarboxylicacid,4-hydroxy-2-methyl-,1,1-dimethylethylester,(2S,4R)-(9CI)

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

213 mg (5.6 mmol) of NaBH4 were added portionwise at 0° C. to a solution of 1.0 g (4.7 mmol) 1-Boc-2-methyl-piperidin-4-on in 10 mL EtOH. The mixture was stirred at room temperature for another 2 h. The solvent was removed by distillation and the remainder was dissolved in water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetated and the combined organic layers were dried over Na2SO4. After filtration the solvent was removed by distillation and the crude product was purified by column chromatography n-heptane/ethyl acetate (1/1) to yield 367 mg (36%) of the cis-isomer 25 and 205 mg (20%) of the trans-isomer 26 in addition to 97 mg (10%) mixture of both isomers.

後処理

  1. customThe solvent was removed by distillation
  2. dissolutionthe remainder was dissolved in water
  3. extractionThe aqueous layer was extracted twice with ethyl
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed by distillation
  7. customthe crude product was purified by column chromatography n-heptane/ethyl acetate (1/1)
  8. customto yield 367 mg (36%) of the cis-isomer 25 and 205 mg (20%) of the trans-isomer 26

出典と根拠

ORDレコード
ord-f0b16671052b4f259bdaae732bc75401
出典データセット
uspto-grants-2014_05
特許番号
US08722671B2

反応ノート

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