1-Benzyloxycarbonyl-3-piperidone → Benzyl 3-hydroxy-3-methylpiperidine-1-carboxylate

HRID 69923노트

반응식

HRID 69923 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.[CH3:18][Mg+].[Br-]>C1COCC1>[OH:1][C:2]1([CH3:18])[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1

참가 물질

4

반응물 2

HCID 15141691-Benzyloxycarbonyl-3-piperidoneHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 10634355Benzyl 3-hydroxy-3-methylpiperidine-1-carboxylate수율 53%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of benzyl 3-oxopiperidine-1-carboxylate (2.33 g, 10 mmol) in dry THF (50 mL) at −78° C. was added MeMgBr (3.6 mL, 3M solution in THF, 11 mmol) slowly. The reaction was allowed to stir at −78° C. for 10 min then slowly warmed to r.t. The reaction was quenched with NH4Cl and dissolved in EtOAc (300 mL) and washed with saturated NH4Cl and brine, dried and filtered, and concentrated to give the crude. The crude material was further purified by silica gel chromatography to yield benzyl 3-hydroxy-3-methylpiperidine-1-carboxylate. (53% yield). LCMS (m/z): 250.1 (MH+); LC Rt=2.98 min.

후처리

  1. temperaturethen slowly warmed to r.t
  2. customThe reaction was quenched with NH4Cl
  3. dissolutiondissolved in EtOAc (300 mL)
  4. washwashed with saturated NH4Cl and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude
  9. customThe crude material was further purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-2e57a71f02f14ccc9ead6aee6a9c6ddc
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822497B2

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