Aluminium lithium hydride → 1-Boc-4-(hydroxymethyl)-4-methylpiperidine

HRID 1986177ノート

反応式

HRID 1986177 の反応式
C[O:2][C:3]([C:5]1([CH3:18])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]([CH2:3][OH:2])([CH3:18])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 463183881-tert-Butyl 4-methyl 4-methylpiperidine-1,4-dicarboxylate

生成物 1

HCID 232828431-Boc-4-(hydroxymethyl)-4-methylpiperidine収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

4-Methylpiperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (1.48 g, 5.73 mmol) is dissolved in THF (15 mL) and cooled to 0° C. 1.0 M lithium aluminum hydride in THF (6.30 mL, 6.30 mmol) is added dropwise. After 1.25 hours the reaction is quenched with MeOH, then stirred with saturated Rochelle's salt until two layers form. The two layers are separated and the aqueous layer is treated with 5 N NaOH and extracted with diethyl ether. The organic layers are combined, concentrated, and chromatographed using silica gel, eluting with EtOAc in hexanes 0-40%, to give the title compound (1.27 g, 97% yield).

後処理

  1. customAfter 1.25 hours the reaction is quenched with MeOH
  2. customThe two layers are separated
  3. additionthe aqueous layer is treated with 5 N NaOH
  4. extractionextracted with diethyl ether
  5. concentrationconcentrated
  6. customchromatographed
  7. washeluting with EtOAc in hexanes 0-40%

出典と根拠

ORDレコード
ord-b3b7a539a342463ebf4536bb346429c8
出典データセット
uspto-grants-2009_06
特許番号
US07547691B2

反応ノート

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