Dichloromethane → tert-Butyl (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate

HRID 1426370ノート

反応式

HRID 1426370 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]2[CH2:14][OH:15])=[CH:4][CH:3]=1.[C:16](=[O:19])([O-])[O-:17].[Na+].[Na+].ClCCl>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][N:11]([C:16]([O:17][C:5]([CH3:8])([CH3:6])[CH3:4])=[O:19])[CH2:10][C@H:9]2[CH2:14][OH:15])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6344Dichloromethane2 回HCID 10340Sodium CarbonateHCID 9855829(3S,4R)-4-(4-Fluorophenyl)-3-piperidinemethanol

生成物 1

HCID 10018204tert-Butyl (3S,4R)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate収率 184.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To a mixture of [(3S,4R)-4-(4-fluorophenyl)piperidine-3-yl]methanol (3.0 g, 14 mmol), sodium carbonate (6.1 g, 57 mmol), dichloromethane (40 mL) and water (40 mL) was added di-tert-butyl Bicarbonate (3.8 g, 17 mmol) under ice cooling, followed by stirring at the same temperature for 30 minutes. The reaction mixture was added to a mixed solution of dichloromethane and water, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:1) to give the title compound (4.0 g, 90% yield).

後処理

  1. customthe organic layer was separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:1)

出典と根拠

ORDレコード
ord-0eb7680ef5ee43f08cff9804d6073cc4
出典データセット
uspto-grants-2015_01
特許番号
US08933100B2

反応ノート

読み込み中…