Tetrahydrofuran → HCID 67371748、化合物

HRID 1677086ノート

反応式

HRID 1677086 の反応式
O1CCCC1.C[O:7][C:8]([C@H:10]1[CH2:15][CH2:14][CH2:13][C@@H:12]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=2)[NH:11]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(OCC)(=O)C.O>[F:22][C:20]1[CH:21]=[C:16]([C@H:12]2[NH:11][C@@H:10]([CH2:8][OH:7])[CH2:15][CH2:14][CH2:13]2)[CH:17]=[C:18]([F:24])[C:19]=1[F:23]

参加物

7

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67372196methyl (2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylate

生成物 1

HCID 67371748HCID 67371748、化合物収率 98.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Under a nitrogen atmosphere, a tetrahydrofuran (10 mL) solution of (2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylic acid methyl ester (3.25 g) was added dropwise at −20° C. into a tetrahydrofuran (50 mL) suspension of lithium aluminum hydride (621 mg). After confirming the disappearance of the raw materials, water (0.62 mL), 5 N sodium hydroxide solution (0.62 mL), and water (1.86 mL) were added in sequence to the reaction solution at the same temperature. After stirring for 15 minutes at the same temperature, ethyl acetate was added, and the resultant was filtered on celite. The filtrate was passed through a silica pad (carrier: Chromatrex NH, eluting solvent: ethyl acetate), and by removing the solvent under a vacuum, the title compound (2.87 g) was obtained. The physical property values are as follows.

後処理

  1. additionwere added in sequence to the reaction solution at the same temperature
  2. additionwas added
  3. filtrationthe resultant was filtered on celite
  4. washThe filtrate was passed through a silica pad (carrier: Chromatrex NH, eluting solvent: ethyl acetate)
  5. customby removing the solvent under a vacuum

出典と根拠

ORDレコード
ord-cc05be737a0148189c265a275420dbea
出典データセット
uspto-grants-2011_08
特許番号
US08008293B2

反応ノート

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