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

HRID 69923ノート

反応式

HRID 69923 の反応式
[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

参加物

4

反応物 2

HCID 15141691-Benzyloxycarbonyl-3-piperidoneHCID 178418689HCID 178418689、化合物

生成物 1

HCID 10634355Benzyl 3-hydroxy-3-methylpiperidine-1-carboxylate収率 53%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2e57a71f02f14ccc9ead6aee6a9c6ddc
出典データセット
uspto-grants-2014_09
特許番号
US08822497B2

反応ノート

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