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

HRID 1516484ノート

反応式

HRID 1516484 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dc2ca8ad771147c682c2400a2f8d2526
出典データセット
uspto-grants-2012_07
特許番号
US08227495B2

反応ノート

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