Hydrochloric Acid → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 29754

反応式

HRID 29754 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](O)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B#B.[H][H].Cl.[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 5

HCID 313Hydrochloric Acid2 回HCID 14798Sodium HydroxideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 6328200DiboronHCID 178418361HCID 178418361、化合物3 回

生成物 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate収率 100.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (19.3 g, 84.0 mmol) in THF (100 mL) was added diborane (185 mL, 1.0 M solution in THF) over a period of 10 min at 0° C. Hydrogen gas was rapidly evolved and after gas evolution had ceased the reaction was stirred at room temperature for 1 h. The reaction mixture was again cooled to 0° C., and 1 M aqueous HCl was added dropwise to the reaction mixture with further evolution of hydrogen. Addition of HCl was continued until the evolution of hydrogen had almost ceased. The mixture was then stirred for 10 min and made basic (pH 13-14) by the addition of 1 M NaOH solution. The aqueous solution was extracted with ethyl acetate, the organic phase washed with brine, dried and concentrated under reduced pressure to yield 4-Hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (18.12 g, 100%).

後処理

  1. temperatureThe reaction mixture was again cooled to 0° C.
  2. stirringThe mixture was then stirred for 10 min
  3. extractionThe aqueous solution was extracted with ethyl acetate
  4. washthe organic phase washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-91d40b688a9b498cabf1e210a690dcf9
出典データセット
uspto-grants-2008_09
特許番号
US07423012B2

関連ノート

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