Tert-butyl 3-benzoylpiperidine-1-carboxylate → tert-Butyl 3-((R)-1-hydroxy-1-phenylhex-5-enyl)piperidine-1-carboxylate

HRID 2266195노트

반응식

HRID 2266195 반응식
[C:1]([CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([Mg]Br)[CH2:23][CH2:24][CH:25]=[CH2:26]>C1COCC1>[OH:8][C@:1]([CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:26][CH2:25][CH2:24][CH:23]=[CH2:22]

참가 물질

4

반응물 2

HCID 57449677Tert-butyl 3-benzoylpiperidine-1-carboxylateHCID 178445862HCID 178445862, 화합물

생성물 1

HCID 67193390tert-Butyl 3-((R)-1-hydroxy-1-phenylhex-5-enyl)piperidine-1-carboxylate수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A stirred solution of tert-butyl 3-benzoylpiperidine-1-carboxylate (160 mg, 0.55 mmol) in dry THF (2 mL) was cooled to −70° C. and 4-pentenylmagnesium bromide in THF (1.8 mL of ˜2.5 M, 2.8 mmol) was added dropwise. The mixture was stirred at −78° C. and allowed to warm to rt overnight. The reaction was quenched with satd aq ammonium chloride. The aqueous layer was extracted with Et2O (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The crude material was purified by flash chromatography on a prepacked silica cartridge eluted with an EtOAc/hexanes gradient. tert-Butyl 3-((R)-1-hydroxy-1-phenylhex-5-enyl)piperidine-1-carboxylate (174 mg, 88%) was isolated as an oil. MS ESI+ve m/z 382 (M+Na)+.

후처리

  1. temperatureto warm to rt overnight
  2. customThe reaction was quenched with satd aq ammonium chloride
  3. extractionThe aqueous layer was extracted with Et2O (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude material was purified by flash chromatography on a prepacked silica cartridge
  9. washeluted with an EtOAc/hexanes gradient

출처 및 근거

ORD 기록
ord-35d4388f1cdd4bc3a4c102d5d3ab1697
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858624B2

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