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

HRID 23958

반응식

HRID 23958 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-69907c3ae526490195aad8c034f65fdb
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855715B1

연결된 노트

불러오는 중…