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

HRID 1254190ノート

反応式

HRID 1254190 の反応式
[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]

参加物

4

反応物 2

HCID 57449677Tert-butyl 3-benzoylpiperidine-1-carboxylateHCID 178445862HCID 178445862、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-84d75d4f1ea44d11ab7df34a8fe4d4d7
出典データセット
uspto-grants-2013_06
特許番号
US08455521B2

反応ノート

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