1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 23958

反応式

HRID 23958 の反応式
[C:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](O)=[O:13])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].B.C1COCC1>C1COCC1>[C:1]([N:8]1[CH2:16][CH2:15][CH:11]([CH2:12][OH:13])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

参加物

4

反応物 2

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 2723981Borane;tetrahydrofuran

生成物 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

1-Boc-isonipecotic acid (10.0 g, 214 mmol) was dissolved in THF (400 mL) and cooled to 0° C. A solution of BH3-THF (180 mL, 1 N in THF, 180 mmol) was added slowly. The mixture stirred for 1 h at 0° C. and was allowed to warm to room temperature for 12 h. The mixture was carefully quenched with water and diluted with ethyl acetate. The water layer was extracted with ethyl acetate. The organic layers were combined, washed with brine, dried (Na2SO4), filtered and concentrated to provide l-Boc-piperidine-4-methanol (7.98 g, 85%) as a white solid.

後処理

  1. temperatureto warm to room temperature for 12 h
  2. customThe mixture was carefully quenched with water
  3. additiondiluted with ethyl acetate
  4. extractionThe water layer was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-69907c3ae526490195aad8c034f65fdb
出典データセット
uspto-grants-2005_02
特許番号
US06855715B1

関連ノート

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