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

HRID 1986177노트

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HRID 1986177 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 232828431-Boc-4-(hydroxymethyl)-4-methylpiperidine수율 97%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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).

후처리

  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%

출처 및 근거

ORD 기록
ord-b3b7a539a342463ebf4536bb346429c8
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547691B2

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