Water → tert-Butyl 3-(3-hydroxypropyl)piperidine-1-carboxylate

HRID 2095430ノート

反応式

HRID 2095430 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15][C:16](O)=[O:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[H][H]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 962WaterHCID 27568241-Boc-piperidin-3-yl-propionic acidHCID 178418361HCID 178418361、化合物

生成物 1

HCID 21188640tert-Butyl 3-(3-hydroxypropyl)piperidine-1-carboxylate収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of commercially available 3-[1-(tert-butoxycarbonyl)-3-piperidinyl]propionic acid (2.57 g, 10.0 mmol) in 100 mL of anhydrous THF was added slowly a solution of BH3.THF complex in THF (1.0 M, 20 mL, 2.0 equiv) at room temperature under N2. The solution was stirred for 16 h at room temperature. Water was added carefully (hydrogen evolution!), and the resulting solution was concentrated under reduced pressure. The residue was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure to give the alcohol (2.35 g, 97%) as a colorless oil. LC-MS (ESI) m/z 244 (M+H+).

後処理

  1. concentrationthe resulting solution was concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-52ae5837b35d4543a226a668dc0e7eca
出典データセット
uspto-grants-2013_05
特許番号
US08445684B2

反応ノート

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