Aluminium lithium hydride → 4-(4-Hydroxymethyl-thiazol-2-yl)-4-methyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 871903노트

반응식

HRID 871903 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[S:16][CH:17]=[C:18]([C:20](OCC)=[O:21])[N:19]=2)([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:15]2[S:16][CH:17]=[C:18]([CH2:20][OH:21])[N:19]=2)([CH3:14])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 579868564-(4-Ethoxycarbonyl-thiazol-2-yl)-4-methyl-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 579868744-(4-Hydroxymethyl-thiazol-2-yl)-4-methyl-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-(4-ethoxycarbonyl-thiazol-2-yl)-4-methyl-piperidine-1-carboxylic acid tert-butyl ester (0.6 g, 1.7 mmol) in anhydrous THF (10 mL) was added LiAlH4 (0.1 g, 2.6 mmol) at 0° C. The mixture was kept at 0° C. for 2 hours and the reaction was quenched with EtOH. The solvent was evaporated and the residue was diluted with EtOAc, washed with 1N NaOH, brine. After drying (Na2SO4), the solvent was removed in vacuo, and the residue was purified by silica column chromatography with EtOAc/hexanes to afford the desired product.

후처리

  1. customthe reaction was quenched with EtOH
  2. customThe solvent was evaporated
  3. additionthe residue was diluted with EtOAc
  4. washwashed with 1N NaOH, brine
  5. dry with materialAfter drying (Na2SO4)
  6. customthe solvent was removed in vacuo
  7. customthe residue was purified by silica column chromatography with EtOAc/hexanes

출처 및 근거

ORD 기록
ord-6aabfff7bd7943e9b82b60a9e12c124f
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975258B2

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